Benzoyl isothiocyanate → N-(1H-benzimidazol-2-ylmethyl)thiourea

Participants

Reaction Steps

To a suspension of 2-(Aminomethyl)benzimidazole dihydrochloride (0.66 g, 3.0 mmol) in dichloromethane (10 mL) was added DIPEA (1.05 mL, 6.0 mmol). The reaction mixture was stirred for 5 minutes and then benzoyl isothiocyante (0.44 mL, 3.3 mmol) was added dropwise. The resulting mixture was stirred for 1 h and then evaporated in vacuo. Ammonia (saturated, in MeOH, 15 mL) was added to the residue. After 4 h the reaction mixture was evaporated. Addition of CH2Cl2 to the residue afforded a solid, which was collected by filtration, washed with dichloromethane and dried to give the title compound (0.38 g, 62%). 1H NMR (DMSO-d6) δ ppm 12.32 (1H), 8.17 (1H), 7.52-7.19 (4H), 4.83 (2H); MS (ESI) m/z 205 (M−1).

Provenance & Evidence