m-Chloroperbenzoic acid → N-(2,4-dimethylphenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2,4-dimethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide (1.27 g, 3.70 mmol) in dichloromethane (DCM) (30 mL) stirred under nitrogen at 0° C., was added meta-chloroperoxybenzoic acid (mCPBA) (2.55 g, 14.79 mmol), portionwise. The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was then stirred for 16 hours at 20° C. DCM (20 mL) was added to the mixture. The organic phase was washed with 0.1M sodium hydroxide solution (2×50 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product. The sample was loaded in dichloromethane and purified on silica (Si) using a 0-50% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 935 mg, as an off-white oil which solidified on standing. LCMS [LCMS1] Rt 1.35 min, m/z (ES+) 360 (M+H).

Provenance & Evidence