Phthaloyl chloride → 2-Ethanethioylisoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a mixture of thioacetamide (10.04 g, 133.64 mmol) and K2CO3 (45.80 g, 331.38 mmol) in 100 ml THF at 0° C. add phthaloyl chloride (28.49 g, 140.32 mmol) dropwise. Raise the reaction temperature to 25° C. after 2 hours and allow it to stir for an additional 2 hours before cooling the reaction mixture to 0° C. again. Quench the reaction by adding 125 mL of ice water dropwise. Extract the reaction mixture with EtOAc (2×). Dry the organic layer with MgSO4 and remove the solvent in vacuo to yield 3.7 g of N-thioacetyl-isoindole-1,3-dione as a crude reddish solid.

Provenance & Evidence