Hydrogen Peroxide → 4-(Oxiran-2-yl)benzene-1-sulfonamide

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Reaction Steps

To a suspension of 4-sulfonamidostyrene (1.83 g, 0.01 mmol) and ammonium hydrogencarbonate (1.6 g, 0.02 mol) in acetonitrile/water (60 mL/30 mL) was added hydrogen peroxide (30% solution, 10 mL, 0.09). The mixture was kept in dark without stirring for 72 hours during which two portion of hydrogen peroxide (5 mL each) were introduced slowly. While HPLC showed all of the starting 4-sulfonamidostyrene was consumed, sodium thiosulfate solution (10%, 60 mL) was added slowly and stirred for 15 minutes. The mixture was extracted with dichloromethane (3×80 mL). The organic phases were combined, washed with brine and dried over magnesium sulfate. The solution was concentrated to give the crude title compound (0.52 g) as an oil.

Provenance & Evidence