Hydrochloric Acid → N-(Diphenylmethyl)-4-nitrobenzenesulfonamide

Participants

Reaction Steps

4-Nitrobenzenesulfonyl chloride (2.51 g) was added to a methylene chloride solution (30 ml) containing benzhydrylamine (2.12 g) and triethylamine (1.62 g) under ice cooling, followed by stirring for 3 hours under ice cooling and for 69 hours at room temperature. Water (30 ml), 1 N hydrochloric acid (12 ml) and methylene chloride (5 ml) were added to the reaction mixture, followed by extraction and solution separation, and the aqueous layer was extracted again with methylene chloride (10 ml). The resulting extract was concentrated, and ethyl acetate (80 ml) and water (50 ml) were further added, followed by solution separation. The organic layer was washed in turn with saturated aqueous solution of sodium bicarbonate (10 ml) and water (25 ml), and concentrated. The resulting solid was washed with a mixed solution of ether (9 ml)/hexane (20 ml) and successively with hexane (10 ml), and dried under vacuum to obtain N-(4-nitrobenzenesulfonyl)benzhydrylamine (3.81 g; yield: 91.3%).

Provenance & Evidence