Potassium Carbonate → N-benzyl-4-methyl-2-(oxazol-5-yl)thiazole-5-carboxamide

反応式

[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([CH:16]=[O:17])=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[O:17][CH:31]=[N:30][CH:29]=2)=[N:13][C:12]=1[CH3:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

実験手順

To a solution of N-benzyl-2-formyl-4-methylthiazole-5-carboxamide (1.09 g, 4.17 mmol) in methanol (60 mL) was added tosylmethyl isocyanide (1.15 g, 5.88 mmol) and potassium carbonate (1.47 g, 10.69 mmol). The reaction mixture was stirred for 50 hours and concentrated in vacuo. The residue was diluted with chloroform and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in 63% yield (1.00 g): 1H NMR (300 MHz, CDCl3) δ 7.95 (s, 1H), 7.70 (s, 1H), 7.42-7.26 (m, 5H), 6.06 (t, J=5.6 Hz, 1H), 4.61 (d, J=5.6 Hz, 2H), 2.72 (s, 3H); MS (ES+) m/z 300.1 (M+1).