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N-[4-phenyl-5-(1,2,4-triazole-1-yl)thiazole-2-yl]amide and preparation and application thereof
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A thiazole and phenyl technology, applied to N-[4-phenyl-5-(1, can solve the problems of high price and strong irritation, and achieve good anticancer activity
Inactive Publication Date: 2016-03-02
HUNAN UNIV
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[0010] In this bromination reaction, NBS has high selectivity, but it has a strong irritant and is relatively expensive
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Embodiment 1
[0037] Preparation of 2-bromo-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone
[0038] Add 0.1mol of 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 3mL of acetic acid, and 0.14mol of sodiumbromide into the reaction flask, and stir at 70°C , add 0.3mol30% hydrogen peroxide dropwise, and react for 3.0h; Rate 85.0%. 1 HNMR (CDCl 3 , 400MHz) δ: 8.80 (s, 1H, triazole 5-H), 8.03 (s, 1H, triazole 3-H), 7.71 (s, 1H, CH), 7.66 (d, J=8.0Hz, 1H , C 6 h 3 6-H), 7.52(d, J=8.0Hz, 1H, C 6 h 3 3-H), 7.44~7.42(m, 1H, C 6 h 3 5-H).
Embodiment 2
[0040] Preparation of 2-bromo-1-(2,4-dichloro-5-fluorophenyl-2-(1,2,4-triazol-1-yl)ethanone
[0041] 0.1mol 1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 3mL acetic acid, 0.14mol sodiumbromide were added to the reaction flask, 70 Stir at ℃, add 0.3mol30% hydrogen peroxide dropwise, react for 3.0h; get 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazole-1 -base) ethyl ketone, yield 88.0%. 1 HNMR (CDCl 3 , 400MHz) δ: 8.76 (s, 1H, triazole 5-H), 8.03 (s, 1H, triazole 3-H), 7.73 (s, 1H, CH), 7.59~7.54 (m, 2H, C6H23, 6-H).
Embodiment 3
[0043] Preparation of 4-(2,4-dichloro-5-fluorophenyl)-5-(1,2,4-triazol-1-yl)thiazol-2-amine
[0044] 1mmol 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanone, 20mL ethanol, reflux, add 1mmo l Thiourea, monitored by TLC, reacted for 10 minutes, cooled to 40°C, added dropwise dilute ammonia water to pH=7-8, and filtered with suction to obtain light yellow solid 4-(2,4-dichloro-5-fluorophenyl)-5- (1,2,4-Triazol-1-yl)thiazol-2-amine, yield 80.3%, m.p.251-253°C. 1 HNMR (CDCl 3 , 400MHz) δ: 8.02 (s, 1H, triazole 5-H), 7.94 (s, 1H, triazole 3-H), 7.49~7.47 (m, 1H, phenyl 3-H), 7.26~7.25 ( m, 1H, phenyl 6-H), 5.78 (s, 2H, NH 2 ).
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technical field [0001] The present invention relates to the preparation and application of novel compounds, specifically the preparation and application of N-[4-phenyl-5-(1,2,4-triazol-1-yl)thiazol-2-yl]amide. Background technique [0002] 2-Bromo-1-phenyl-2-(1,2,4-triazol-1-yl)ethanone is the preparation of 4-phenyl-5-(1,2,4-triazol-1-yl) - The key intermediate of 1,3-thiazol-2-amine and its derivatives. The preparation of 2-bromo-1-phenyl-2-(1,2,4-triazol-1-yl)ethanone and its use in the synthesis of thiazole derivatives has been described [J.Organomet.Chem. 2006, 691: 2686; Synth.Commun.2007, 37: 199; HeteroatChem 2007, 18: 55; Chemical Journal of Higher Schools, 2007, 28: 270-273; Organic Chemistry, 2012, 32: 1715-1718]. Fang Jianxin et al. describe bromination of 1-phenyl-2-(1,2,4-triazol-1-yl)ethanone with molecular bromine in acetic acid to obtain 2-bromo-1-phenyl-2-(1 , 2,4-triazol-1-yl) ethanone; The preparation reaction is as follows: [0003] [0004] In th...
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