Water → 2,3-Dioxoindoline-5-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

A mixture of isatinsulfonic acid sodium salt hydrate (10.00 g, 39.7 mmol ) and phosphorous oxychloride (18.5 mL, 199 mmol, 5 eq) in tetramethylene sulfone (50 mL) was heated at 60° C. for 3 hours under a dry N2 atmosphere. The reaction was cooled in an ice bath to 0 C. and water was cautiously added drop-wise, keeping the internal temperature below 6° C. The resulting green solid was collected by filtration and was washed well with water. The solid was dissolved in ethyl acetate (200 mL) and washed again with water (3×50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude product in 85% yield. The solid was recrystallized from ethyl acetate: hexanes with hot filtration to give the title compound (5.81 g, 66% yield). NMR (400 MHz, DMSO-d6): consistent.

Provenance & Evidence