Water → HCID 86591569、化合物

反応式

[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[H-].[Na+].Br[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.O.[CH3:28]N(C)C=O>>[CH3:28][CH:1]([NH:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1)[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1

参加物

反応物 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 12081Methyl 4-bromobenzoate

HCID 24758Sodium hydride

HCID 824443N-methyl-4-phenylthiazol-2-amine

生成物 1

HCID 86591569HCID 86591569、化合物収率 86%

実験手順

To a solution of 2-methylamino-4-phenylthiazole (1.76 g) in N,N-dimethylformamide (25 mL) was gradually added sodium hydride (60%, oil, 351 mg) at room temperature and the mixture was stirred for 30 min. Methyl 4-bromobenzoate (2.11 g) was added, and the mixture was further stirred for 1.5 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzoate (2.56 g, 86%) as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v).