Dimethylformamide → HCID 68491182, compound

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (0.75 mL) and DMF (catalytic amount) were added to a solution of N-(5-indanyl)-3(phenylthio)acrylamide (1.21 g) in toluene (50 mL) at room temperature, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added THF (40 mL), and then a solution (0.62 mol/L, 10 mL) of phenylmercaptan sodium salt in THF was added thereto under ice-cooling. The mixture was stirred at room temperature for 2 hours, and then alkalilized by addition of a 1N aqueous sodium hydroxide solution, followed by extraction with ethyl acetate (250 mL). The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=100:1 to 50:1) to obtain phenyl N-(5-indanyl)-3-(phenylthio)thioacrylimidate (Z-isomer: 0.27 g, E-isomer: 0.94 g).

Provenance & Evidence