HCID 68494041, compound → N-benzyl-2-cyano-4-methylthiazole-5-carboxamide

Reaction equation

[Cu][C:2]#[N:3].[CH2:4]([NH:11][C:12]([C:14]1[S:18][C:17](I)=[N:16][C:15]=1[CH3:20])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C)C=O.O>[CH2:4]([NH:11][C:12]([C:14]1[S:18][C:17]([C:2]#[N:3])=[N:16][C:15]=1[CH3:20])=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Procedure

To a stirred mixture of copper(I) cyanide (0.19 g, 2.10 mmol) in anhydrous N,N-dimethylformamide (6 mL) at 150° C. was added N-benzyl-2-iodo-4-methylthiazole-5-carboxamide (0.30 g, 0.84 mmol). The resulting reaction mixture was stirred at same temperature for 10 minutes, and then allowed to cool to ambient temperature and diluted with water (50 mL). The resulting precipitate was filtered, washed with water (50 mL) and ethyl acetate (100 mL). The organic filtrate was washed with water (2×50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-20% ethyl acetate in hexanes) to afford the title compound as a clear oil (0.09 g, 39%): 1H NMR (300 MHz, CDCl3) δ 7.42-7.30 (m, 5H), 6.17 (br s, 1H), 4.63 (d, J=5.6 Hz, 2H), 2.73 (s, 3H); MS (ES−) m/z 256.2 (M−1).