Mục tiêu nghiên cứu đề tài này là từ chất đầu ophenylenediamine, tiến hành khép vòng benzimidazol với cacbonđisunfua và kali hidroxit để thu được 2–mercaptobenzimidazole. Tiếp tục, cho hợp chất trên tác dụng với các cloroacetamide thế khác nhau để thu được dãy các amide có chứa dị vòng 2 mercaptobenzimidazole; nghiên cứu tính chất và cấu trúc các chất tổng... Đề tài Hoàn thiện công tác quản trị nhân sự tại Công ty TNHH Mộc Khải Tuyên được nghiên cứu nhằm giúp công ty TNHH Mộc Khải Tuyên làm rõ được thực trạng công tác quản trị nhân sự trong công ty như thế nào từ đó đề ra các giải pháp giúp công ty hoàn thiện công tác quản trị nhân sự tốt hơn trong thời gian tới.
TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC PHẠM XN PHÚ KHĨA LUẬN TỐT NGHIỆP Chun ngành: Hóa hữu ĐỀ TÀI: 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a TỔNG HỢP MỘT SỐ AMIDE CHỨA DỊ VÒNG 2-MERCAPTOBENZIMIDAZOLE 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d Tháng năm 2012 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 TRƯỜNG ĐẠI HỌC SƯ PHẠM TP.HCM KHOA HÓA HỌC KHĨA LUẬN TỐT NGHIỆP Chun ngành: Hóa hữu ĐỀ TÀI: TỔNG HỢP MỘT SỐ AMIDE CHỨA DỊ VÒNG 2-MERCAPTOBENZIMIDAZOLE 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b GVHD: TS NGUYỄN TIẾN CÔNG f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 SVTH: PHẠM XUÂN PHÚ 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e KHÓA: 34 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Tháng năm 2012 LỜI CẢM ƠN Khóa luận tốt nghiệp hồn thành, ngồi cố gắng thân, em cịn nhận nhiều giúp đỡ, động viên từ gia đình, thầy cơ, bạn bè Trước hết, em xin gửi lời cảm ơn chân thành đến thầy Nguyễn Tiến Cơng - tận tình bảo, hướng dẫn giúp đỡ em suốt thời gian thực khóa luận Em xin chân thành cảm ơn đến ban chủ nhiệm khoa Hóa, thầy tổ Hóa Hữu Cơ nói riêng khoa Hóa nói chung tạo điều kiện thuận lợi cho em suốt q trình thực khóa luận Và cuối cùng, em xin cám ơn nhiệt tình giúp đỡ, động viên gia đình bạn làm khóa luận Trong thời gian thực đề tài, có nhiều lần thất bại có nhiều niềm vui tổng hợp thành công chất giúp em tiếp thu nhiều kiến thức bổ ích, rèn luyện kỹ làm thí nghiệm…Tuy nhiên, khả cịn hạn chế nên khơng thể tránh khỏi sai sót mong góp ý thầy bạn để đề tài hoàn thiện Em xin chân thành cảm ơn Thành phố Hồ Chí Minh, tháng năm 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e 2012 e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a Sinh viên 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc Phạm Xuân Phú c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 MỤC LỤC MỤC LỤC 02 LỜI MỞ ĐẦU 05 CHƯƠNG I: TỔNG QUAN 07 I.1 BENZIMIDAZOLE 08 I.1.1 Giới thiệu chung 08 I.1.2 Hiện tượng tautomer hóa vịng benzimidazole 09 I.2 TỔNG HỢP BENZIMIDAZOLE 10 I.2.1 Từ O-phenylenediamine 10 I.2.2 Từ benzimidazole khác 15 I.2.3 Từ phương pháp tổng hợp khác 16 I.2.4 Tổng hợp 2-mercaptobenzimidazole 17 I.3 TÍNH CHẤT CỦA CÁC BENZIMIDAZOLE 19 I.3.1 Tính chất vật lí 19 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e I.3.2 Tính chất hóa học 22 e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b I.4 HOẠT TÍNH SINH HỌC CỦA BENZIMIDAZOLE 28 f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b I.5 ỨNG DỤNG CỦA BENZIMIDAZOLE 30 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 CHƯƠNG II: THỰC NGHIỆM 32 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 II.1 SƠ ĐỒ THỰC NGHIỆM 33 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 II.2 QUI TRÌNH THỰC HIỆN 33 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b II.2.1 Tổng hợp 2-Mercaptobenzimidazole (A2) 33 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d II.2.2 Tổng hợp amide dị vòng 2-mercaptobenzimidazole 35 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a II.3 XÁC ĐỊNH CẤU TRÚC VÀ MỘT SỐ TÍNH CHẤT 39 II.3.1 Xác định nhiệt độ nóng chảy 39 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 II.3.2 Phổ hồng ngoại (IR) 39 II.3.3 Phổ cộng hưởng từ proton ( 1H-NMR) 39 II.3.4 Thăm dị hoạt tính sinh học 39 CHƯƠNG III: KẾT QUẢ VÀ THẢO LUẬN 40 III.1 Tổng hợp 2-Mercaptobenzimidazole (A2) 42 III.1.1 Cơ chế phản ứng 42 III.1.2 Phân tích phổ 44 III.2 Tổng hợp 2-[(benzimidazol-2-yl)thio]-N-phenylacetamide (A3) 46 III.2.1 Cơ chế phản ứng 46 III.2.2 Phân tích phổ 47 III.3 Tổng hợp 2-[(benzimidazol-2-yl)thio]-N-(4-nitrophenyl)acetamide (A4) 50 III.3.1 Cơ chế phản ứng 50 III.3.2 Phân tích phổ 50 III.4 Tổng hợp 2-[(benzimidazol-2-yl)thio]-N-(p-tolyl)acetamide (A5)……… 53 III.4.1 Cơ chế phản ứng 53 III.4.2 Phân tích phổ 53 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e III.5 Tổng hợp 2-[(benzimidazol-2-yl)thio]acetamide (A6) 55 e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b III.5.1 Cơ chế phản ứng 55 f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b III.5.2 Phân tích phổ 55 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 III.6 Hoạt tính sinh học 58 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 CHƯƠNG IV: KẾT LUẬN VÀ ĐỀ XUẤT 61 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b TÀI LIỆU THAM KHẢO 62 f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e PHỤ LỤC 65 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 LỜI MỞ ĐẦU Trong năm gần đây, hóa học dị vòng ngày phát triển mạnh mẽ Việc tổng hợp nghiên cứu hợp chất dị vòng thu hút ý nhiều nhà hóa học Người ta quan tâm đến dị vịng khơng tính chất lí hóa học đặc biệt mà ứng dụng quan trọng chúng thực tiễn Một số dị vòng nhận quan tâm nhiều tác giả dị vòng benzimidazole Các dẫn xuất chứa dị vòng benzimidazole trở thành đối tượng nghiên cứu hấp dẫn dược tính, hoạt tính sinh học ứng dụng chúng Theo số báo cáo, dẫn xuất có khả làm giảm đau, diệt giun sán, kháng khuẩn, chống lỡ loét viêm nhiễm vết thương, chống tăng huyết áp, kháng virus HIV… Đặc biệt, dẫn xuất 2–mercaptobenzimidazole – dẫn xuất quan trọng benzimidazole – có hàng loạt hoạt tính sinh học quý như: kháng khuẩn, kháng histamine, giảm đau Mặt khác, amide nhóm hoạt chất có nhiều dược tính kháng khuẩn, kháng nấm, chống viêm nhiễm, thành phần thuốc chống trầm cảm, rối loạn thần kinh có tác dụng hạ sốt Từ vấn đề nêu trên, chọn đề tài: “TỔNG HỢP MỘT SỐ AMIDE CỦA DỊ VÒNG 2- 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a MERCAPTOBENZIMIDAZOLE” 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b Mục tiêu đề tài là: dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca Từ chất đầu o-phenylenediamine, tiến hành khép vòng benzimidazol với cacbonđisunfua kali hidroxit để thu 2–mercaptobenzimidazole Tiếp tục, cho e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 hợp chất tác dụng với cloroacetamide khác để thu dãy amide có chứa dị vòng 2- mercaptobenzimidazole 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 Nghiên cứu tính chất cấu trúc chất tổng hợp thơng qua nhiệt độ nóng 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e chảy phổ IR, H-NMR Sau đó, tiến hành thăm dị hoạt tính sinh học amide vừa tổng hợp 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 CHƯƠNG I:TỔNG QUAN 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 I.1 BENZIMIDAZOLE I.1.1 Giới thiệu chung Dị vịng benzimidazole có chứa vịng benzen kết hợp với vịng imidazole N N H Các nhà hóa học nghiên cứu benzimidazole khám phá 5,6 – dimetylbenzimidazole nằm thành phần cấu trúc vitamin B 12 Trong lịch sử, dị vịng benzimidazole tìm năm 1872 Hoebrecker [24] Ông thu 2,5 (hoặc 2,6)-dimethylbenzimidazole phản ứng khử 2-nitro-4metylacetanilide H3C NO2 H3C Sn NHCOCH3 NH2 -H2O NHCOCH3 HCl 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b H N H N H3C dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca CH3 CH3 hay N e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 N H3C 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b Một vài năm sau đó, Ladenburg [38] thu hợp chất phản ứng ngưng tụ 3,4 – diaminotoluen với axit acetic f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 H3C NH2 -H2O H3C NH2 + CH3COOH -H2O 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d II 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 NH2 NHCOCH3 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Những hợp chất loại hình thành từ nước nên gọi bazơ khan nước [26,27,28] Benzimidazole biết đến dị vòng benzimidazole benzoglyoxaline Chúng đặt tên từ dẫn xuất o-phenylenediamine Khi 2methylbenzimidazole gọi ethenyl-o-phenylenediamine Chúng đặt tên dẫn xuất nhóm chức vỏng imidazole Ví dụ: Benzimidazole gọi o-phenylformamidine Và (3H) – benzimidazolone (1) (3H)- benzimidazolethione (2) gọi o-phenyleneurea ophenylenethiourea H N H N S O N H N H (1) (2) Quy tắc đánh số vòng benzimidazole sau: H N 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b N f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b Đăc biệt, vị trí thứ rõ vị trí –μ 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 I.1.2 Hiện tượng tautome hóa benzimidazole 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 Benzimidazole chứa nguyên tử hidro liên kết với nitơ vị trí số dễ bị tautome 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 hóa Điều miêu tả sau [18]: df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e N H N 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 N H N 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Sự tautome hóa tương tự imidazole amidine Mặc dù, có cơng thức viết chất Điều chứng tỏ với (hoặc 6) – methylbenzimidazole H3C N H3C N H (3) H N N (4) Vì vậy, 5-methylbenzimidazole (3) tautome 6-methylbenzimidazole (4) cấu trúc (3 4) hợp chất I.2 TỔNG HỢP BENZIMIDAZOLE I.2.1 Từ O-phenylenediamine I.2.1.1 Phản ứng với acid cacboxylic a Phản ứng với monoacid O–phenylenediamine phản ứng dễ dàng với tất axit cacboxylic tạo thành 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e benzimidazole với nhóm vị trí số Phản ứng hiệu suất cao Phản ứng e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a thực cách đun nóng hỗn hợp chất phản ứng bình cầu lắp sinh hàn hay ống kín Acid sử dụng không cần thiết axit khan 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca H N NH2 e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 + RCOOH NH2 R + H2O N 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 Phản ứng đạt hiệu suất 83% - 85% dùng acid fomic 90% nồng độ acid fomic thấp (25%) thành cơng Khi dùng acid axetic hợp chất tổng hợp 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 2-methylbenzimidazole (H = 68%) [13] 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 Acid acrylic không tạo –vinylbenzimidazole Thay vào hình thành 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 hợp chất vòng cạnh Phụ lục 2: Phổ 1H-NMR 2-mercaptobenzimidazole (A2) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 3: Phổ 1H-NMR dãn rộng 2-mercaptobenzimidazole (A2) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 4: Phổ IR 2-[(benzimidazol-2-yl)thio]-N-phenylacetamide (A3) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 5: Phổ 1H-NMR 2-((benzimidazol-2-yl)thio)-N-phenylacetamide (A3) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 6: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]-N-phenylacetamide (A3) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 7: Phổ IR 2-[(benzimidazol-2-yl)thio]-N-(4-nitrophenyl)acetamide (A4) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 8: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]-N-(4-nitrophenyl)acetamide (A4) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 9: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]-N-(4-nitrophenyl)acetamide (A4) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 10: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]-N-(4-nitrophenyl)acetamide (A4) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 11: Phổ IR 2-[(benzimidazol-2-yl)thio]-N-(p-tolyl)acetamide (A5) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 12: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]-N-(p-tolyl)acetamide (A5) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 13: Phổ 1H-NMR dãn rộng 2-[(benziAmidazol-2-yl)thio]-N-(p-tolyl)acetamide (A5) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 14: Phổ IR 2-[(benzimidazol-2-yl)thio]acetamide (A6) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 15: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]acetamide (A6) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Phụ lục 16: Phổ 1H-NMR dãn rộng 2-[(benzimidazol-2-yl)thio]acetamide (A6) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77