Ammonium Hydroxide → HCID 178502021, compound

Participants

Reaction Steps

The above hydrochloride salt of methyl (±)-[5- [chloro (phenyl)methyl]-1H-benzimidazol-2-yl]carbamate was then suspended in dry tetrahydrofuran (30 mL) and excess ammonium hydroxide was added to this suspension. The resulting reaction mixture was stirred at room temperature for 12 hours. The solvent was then removed and the residue was chromatographed on silica gel 60F254 (40 g, 70-230 mesh, column size 1'×1") using CHCl3 :CH3OH (95:5) as eluant. Fractions 3 through 12 (20 mL each) upon concentrating on a steam bath under vacuum afforded the title product, yield 22%; mp>232° C.; IR (KBr): 3340, 1718, 1630, 1600, 870, 750, 721, 695 cm-1. 1H-NMR (DMSO-d6): δ 3.75 (2, 3H, --OCH3); 5.23 (2, 1H, CH--N), 5.60-6.87 (m, 2H, NH2 [exchangeable with D2O]), 6.90-7.83 (m, 9H, Ar--H and NHCO [exchangeable with D2O]). Analysis calculated for C16H16N4O2 : C, 64.85; H, 5.44; N, 18.91 and found: C, 65.03; H, 5.53; N, 18.67.

Provenance & Evidence