Ethylene Oxide → 2-(2-hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

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Reaction Steps

To approximately 2 ml of ethylene oxide cooled in an ice bath was added a suspension of 4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide (2.0 g, 8.76 mmol) in H2O (140 ml). After stirring in the ice bath for 1 hour, the mixture was allowed to stir at 20-25° for 18 hours. Water was removed under reduced pressure and the residue flash chromatographed over silica gel. Elution with 2% isopropanol-98% CH2Cl2 gave product which was recrystallized from EtOAc-hexane to give the 2-hydroxethyl derivative (0.39 g, 16%), m.p. 140-1°.

Provenance & Evidence