Carbon Disulfide → Ethyl 2-cyano-3,3-bis(benzylthio)acrylate

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, sodium hydride (60%, 6.77 g) was added to dimethylformamide (75 mL). Thereto was added dropwise a solution of ethyl cyanoacetate (9.57 g) in dimethylformamide (15 mL) under cooling (internal temperature: ca. 10° C.) over a period of 15 minutes, and the mixture was stirred at room temperature for 10 minutes. Thereto was added dropwise a solution of carbon disulfide (5.09 mL) in dimethylformamide (12 mL) under cooling (internal temperature ≦10° C.) over a period of 20 minutes. The mixture was stirred at room temperature overnight, and thereto was added dropwise a solution of benzyl bromide (20.1 mL) in dimethylformamide (23 mL) under cooling (internal temperature ≦25° C.). The mixture was stirred at 70° C. for 7 hours and at room temperature overnight. The reaction mixture was poured in ice-water, and the mixture was stirred. The precipitates were collected by filtration and recrystallized from hot ethanol. The resultant crystals were washed with cold ethanol to give ethyl 2-cyano-3,3-bis(benzylthio)acrylate (25.63 g, yield: 82%) as a colorless solid.

Provenance & Evidence