Potassium Bicarbonate → N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-benzenesulfonyl-3-amino-4-acetylaminobenzamide potassium salt (0.500 g), 4-benzyloxybenzyl bromide (0.470 g), 20% potassium bicarbonate aqueous solution (0.925 g) and N,N-dimethylformamide (3 ml) is stirred for one hour at 90° C. The reaction solution is concentrated and purified through silica gel column chromatography (eluate: ethyl acetate/methanol=9/1) to obtain preliminarily purified N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide. This material underwent cyclization and thus, 6-benzenesulfonylcarbamoyl-1-(4-benzyloxybenzyl)-2-methylbenzimidazole (0.160 g) is obtained. 1H-NMR (DMSO-d6, δ): 2.54 (3H, s), 5.05 (2H, s), 5.44 (2H, s). 7.09 (2H, d, J=8.7 Hz), 7.32 (2H, d, J=7.0 Hz), 7.29-7.44 (5H, m), 7.58-7.67 (3H, m), 7.68-7.75 (2H, m), 7.79-8.02 (2H, m), 8.18 (1H, s), 12.46 (1H, s).

Provenance & Evidence