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

Participants

Reaction Conditions

Reaction Steps

To a mixture of thioacetamide (10.04 g, 133.6 mmol) and potassium carbonate (45.80 g, 331.4 mmol) in 100 mL tetrahydrofuran at 0° C. add phthaloyl chloride (28.49 g, 140.3 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 magnesium sulfate and remove the solvent in vacuo to yield 3.7 g of 2-thioacetylisoindole-1,3-dione as a crude reddish solid. See also J. Org. Chem. 1997, 62, 3808-3809. 1H NMR (CDCl3) δ 8.00 (2 H, m), 7.82 (2 H, m), 3.10 (3 H, s).

Provenance & Evidence