Methane → (5-nitro-1H-1,3-benzodiazol-2-yl)methanol

Participants

Reaction Steps

1,2-Diamino-4-nitrobenzene (5.00 g, 0.0326 mol), glycolic acid (3.72 g, 0.0490 mol), 4.00 M hydrogen chloride in water (13.1 mL, 0.0522 mol), water (13.1 mL, 0.725 mol), and activated charcoal (100 mg) were refluxed overnight. The reaction was cooled to room temperature, filtered and neutralized with aqueous ammonia. The product was filtered and dried in a vacuum desiccator overnight to obtain (6-nitro-1H-benzoimidazol-2-yl)-methanol as a brown solid (6.29 g, 100%). m.p.=157-162° C.; LCMS (m/e) 194 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 10.24 (bs, 1H), 8.39 (d, 1H, J=1.9 Hz), 8.09 (dd, 1H, J=1.9 and 8.8 Hz), 7.66 (d, 1H, J=8.8 Hz), 5.93 (bs, 1H), 4.77 (s, 2H).

Provenance & Evidence