Toluene → HCID 67543919, compound

Participants

Reaction Steps

A mixture of 3.68 g (13 mmol) of 2-ethyl-N-phenyl-3-(phenylthio)-2-propenamide, 1.9 ml (26 mmol) of thionyl chloride, 10 mg of DMF, and 20 ml of toluene was refluxed for 1 hour. After concentration of the mixture under vacuum, the residue was dissolved in 35 ml of DMF and then 2.0 g (15.1 mmol) of a benzenethiol sodium salt was added portionwise under ice cooling and stirred at room temperature for 1 hour. After dilution with tert-butyl methyl ether, the mixture was washed sequentially with water (three times) and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 2.03 g of phenyl 2-ethyl-N-phenyl-3-(phenylthio)-2-propenimidothioate (hereinafter referred to as the present compound 14).

Provenance & Evidence