Water → 6-Methylthio-2-oxindole-1-carboxamide

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Reaction Steps

Chlorosulfonyl isocyanate (5.66 g, 0.04 mole) was added to a slurry of 6-methylthio-2-oxindole (6.0 g, 0.033 mole) in acetonitrile (60 ml) at 5° to 10° C. The reaction mixture was stirred for one hour. Water (100 ml) was then added and stirring was continued for ten minutes. The aqueous solution was extracted with ethyl acetate (600 ml), which was then washed successively with water and brine, dried (MgSO4) and evaporated under reduced pressure to give a gray solid which was recrystallized from acetonitrile. Yield=3.0 g. An additional 0.71 g of product was obtained from the mother liquor. Total yield=3.71 g (50.6%); m.p. 176°-179° C.

Provenance & Evidence