o-Mesitylenesulfonyl HydroxylaMine

773-64-8

58042-39-0

GENERAL METHOD: Hydroxylamine hydrochloride (2 eq.) and DMAP (2 eq.) were dissolved in pyridine (20 mL) in an ice bath and 2,4,6-trimethylbenzenesulfonyl chloride (1 eq.) was slowly added. The reaction mixture was stirred at room temperature for 5 minutes. The resulting suspension was poured into a mixture of ethyl acetate (100 mL) and 1N aqueous hydrochloric acid (100 mL). The organic layer (ethyl acetate layer) was separated, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by fast column chromatography under the following gradient conditions and recrystallized from a mixed ether/hexane solvent to give N-hydroxy-2,4,6-trimethylbenzenesulfonamide.