Benzylamine → N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Participants

Reaction Steps

To a solution of 2-amino-4-methylthiazole-5-carboxylic acid (0.86 g, 5.44 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1-hydroxy-benzotriazole (0.96 g, 7.07 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.36 g, 7.07 mmol), N,N-diisopropylethylamine (2.46 mL, 14.14 mmol) and benzylamine (0.71 mL, 6.53 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (20-35% ethyl acetate in hexanes) to afford the title compound as a white solid (1.02 g, 76%): 1H NMR (300 MHz, DMSO-d6) δ 8.01 (t, J=6.0 Hz, 1H), 7.36-71.9 (m, 7H), 4.34 (d, J=6.0 Hz, 2H), 2.34 (s, 3H); MS (ES+) m/z 248.2 (M+1).

Provenance & Evidence