Reaktion #51953

Reaktionsgleichung

hydrogen peroxide

4-sulfonamidostyrene

ammonium hydrogencarbonate

4-sulfonamidostyrene

hydrogen peroxide

→

crude title compound

4-Oxiran-2-ylbenzenesulfonamide

Lösungsmittel

acetonitrile water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere introduced slowly
2. 2
   Sonstigewas consumed
3. 3
   workup.ADDITIONsodium thiosulfate solution (10%, 60 mL) was added slowly
4. 4
   ExtraktionThe mixture was extracted with dichloromethane (3×80 mL)
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   EinengenThe solution was concentrated

Vorschrift

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.

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