Water → HCID 178419600, compound

Participants

Reaction Steps

3,4-Diaminobenzoic acid methyl ester (58.72 mmoles, 9.35 g, 1 equivalent, commercially available from Oakwood Products) was dissolved in acetonitrile (20 ml) and water (200 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (8.64 g, 81.55 mmoles, 1.4 equivalent) was added over a period of 5 minutes, and the reaction mixture was allowed to go to room temperature and stirred for 16 hours. The reaction mixture was then evaporated under reduced pressure to 15.60 g of methyl 2-amino-1H-benzo[d]imidazole-5-carboxylate hydrobromide (yield: 98%) which was used directly in the next reaction without any further reaction. 1H-NMR (400 MHz DMSO-d6) δ 12.64 (br s, 2H), 8.80 (bs, 3H), 7.91 (s, 1H), 7.82 (d, 1H), 7.51 (d, 1H), 3.82 (s, 3H). MS (EI): 192 (MH+).

Provenance & Evidence