2-Nitrobenzenesulfonyl chloride → N-(Benzyloxy)-2-nitrobenzenesulfonamide

Participants

Reaction Steps

A solution of 2-nitrobenzene-1-sulfonyl chloride (500 g, 2.26 mol) in pyridine (1500 mL) was added dropwise to a 0° C. solution of O-benzylhydroxylamine hydrochloride (400 g, 2.51 mol) in pyridine (1500 mL). The reaction mixture was allowed to warm to room temperature then was stirred at 20° C. overnight. The mixture was concentrated under reduced pressure, diluted with DCM and washed with HCl (10%, 3×). The combined organic layer was concentrated under reduced pressure and re-crystallized with DCM to afford N-(benzyloxy)-2-nitrobenzenesulfonamide (485 g, 62.6%) as a yellow solid.

Provenance & Evidence