Dimethylformamide → S-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] ethanethioate

Participants

Reaction Steps

0.855 kg (7.9M) Potassium-tert-butoxide is added in portions at -5° under nitrogen atmosphere to 4 1 dimethylformamide. A solution of 0.6 kg (7.9M) thioacetic acid in 2 1 dimethylformamide is added in a steady stream at such a rate that the temperature can be maintained between -5° and 0° . The reaction mixture is then stirred for 1 hour at -5° . 2.0 kg (7.9M) N-(2-bromoethyl)phthalimide in 4 1 dimethylformamide is added to the reaction mixture at such a rate that the temperature does not exceed 5° and the reaction mixture is stirred for 2 hours. 40 1 of water cooled at 5°-10° are added which raises the reaction temperature to 20° . The reaction mixture is stirred overnight at room temperature and filtered. The crude product is washed with water and dried. M.P. 112°-114°.

Provenance & Evidence