Phosphorus oxychloride → 2,3-Dioxoindoline-5-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

To a mixture of isatinsulfonic acid, sodium salt dihydrate (10 g, 35.1 mmol) and 50 mL tetramethylene sulfone was added phosphorus oxychloride (16.5 mL, 177 mmol). The resulting mixture was heated at 60° C. for 3 hours. The mixture was cooled to 0° C. and 120 mL of water was cautiously added. The resulting green solid was filtered and washed with water. The solid was dissolved in 100 mL EtOAc and washed thrice with 50 mL of water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow solid. The solid was recrystallized from EtOAc/Hexanes to give the title compound as an orange solid (5.2 g, 60.5%). ES (−) MS m/e=344 (M−H).

Provenance & Evidence