Potassium Carbonate → N-benzyl-2-(5-benzyl-1H-1,2,4-triazol-3-yl)-4-methylthiazole-5-carboxamide

Participants

Reaction Steps

A mixture of N-benzyl-2-cyano-4-methylthiazole-5-carboxamide (0.085 g, 0.33 mmol), phenylacetic hydrazide (0.02 g, 0.13 mmol) and potassium carbonate (0.037 g, 0.27 mmol) in 1-butanol (2 mL) was subjected to a microwave irradiation (150° C., 100 W) for 30 minutes. The reaction mixture was purified by column chromatography (0-10% methanol in dichloromethane). Less polar fractions were combined and concentrated in vacuo. The residue was purified by preparative thin layer chromatography plate (60% ethyl acetate in hexanes) to afford the title compound as a yellow solid (0.007 g, 15%): mp 235-237° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.87 (t, J=5.6 Hz, 1H), 7.38-7.21 (m, 11H), 4.43 (d, J=5.6 Hz, 2H), 4.15 (s, 2H), 2.61 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 160.8, 156.8, 155.4, 139.1, 136.4, 128.6, 128.6, 128.3, 127.2, 126.8, 42.7, 31.7, 17.0; MS (ES+) m/z 390.3 (M+1).

Provenance & Evidence