Phenyl Isothiocyanate → 2-Phenylthio-2-(3-phenyl-1,3-thiazolidine-2-yliden)acetonitrile

Participants

Reaction Steps

18.9 g (140 mmols) of phenylisothiocyanate and 20.9 g (140 mmols) of phenylthioacetonitrile dissolved in 50 ml of dimethylformamlde were added dropwise with stirring at room temperature to a suspension of 11.5 g of sodium hydride (60% oil, 287 mmols) in 200 ml of dimethylformamide. The mixture was stirred for 1 hour, and 28.9 g (154 mmols) of 1,2-dibromoethane was added dropwise at room temperature. Then the mixture was stirred for 3 hours. To the reaction mixture were added 300 ml of water and 100 ml of ether, followed by stirring. The precipitated crystals were collected by filtration, giving 26.1 g of the title compound as colorless crystals (yield 60%).

Provenance & Evidence