2-Chlorobenzimidazole → 2-Aminobenzimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-aminobenzylamine (500 mg, 4.1 mmol) and 2-chlorobenzoimidazole (305 mg, 2.0 mmol) was heated at 110° C. for 18 h. The resulting solid was dissolved in CH2Cl2 (30 mL) and washed with H2O (30 mL). The organic layer was separated, dried over Na2SO4, and concentrated to provide crude benzimidazole-amine (200 mg) which was treated with CDI (500 mg, 3.0 mmol) in anhydrous DMF (15 mL). After stirring at RT for 18 h, the reaction mixture was concentrated and the viscous residue was triturated with CH2Cl2. The precipitates were filtered and recrystallized from DMSO (3 mL) and CH2Cl2 (0.5 mL) to afford the title compound as an off-white solid. MS m/z: 265 (M+H+). Anal. Calc'd for C15H12N4O: C, 68.17; H, 4.58; N, 21.20; O, 6.05; Found C, 68.35; H, 4.71; N, 21.27; O, 6.04.

Provenance & Evidence