O-Phenylenediamine → 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol

Participants

Reaction Conditions

Reaction Steps

A mixture of benzene-1,2-diamine (500 mg, 4.6 mmol), 5-chloro-2-methoxy-benzoic acid (1.3 g, 6.9 mmol) in PPA (30 mL) was allowed to stir at 200° C. for 5 hours. The mixture was poured to ice and neutralized with KOH. The mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. The organic phase was concentrated to provide 2-(1H-benzo[d]imidazol-2-yl)-4-chlorophenol (300 mg, yield: 27%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.20 (d, J=2.5 Hz, 1H), 7.73˜7.70 (m, 2H), 7.44 (dd, J=8.8, 2.6 Hz, 1H), 7.34˜7.32 (m, 2H), 7.10 (d, J=8.8 Hz, 1H). MS (M+H)+: 245.

Provenance & Evidence