Aniline → (E)-2-methyl-N-phenyl-3-(phenylthio)-2-propenamide

Reaction equation

[CH3:1]/[C:2](=[CH:6]\[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[C:3]([OH:5])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[CH3:1]/[C:2](=[CH:6]\[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[C:3]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:5]

Participants

Procedure

A suspension of 2.5 g (12.8 mmol) of (E)-2-methyl-3-(phenylthio)-2-propenoic acid and 3.5 g (25.7 mmol) of thionyl chloride in 25 ml of toluene was refluxed for 1 hour and then concentrated under vacuum. The residue was dissolved in 25 ml of ethyl acetate and cooled in ice bath. To the solution was added dropwise 2.9 g (32 mmol) of aniline and stirred at room temperature for 30 minutes. The reaction mixture was washed sequentially with 1N HCl solution, a saturated NaHCO3 solution, and a saturated NaCl solution. The organic layer was dried over anhydrous MgSO4 and concentrated to obtain 3.0 g of (E)-2-Methyl-N-phenyl-3-(phenylthio)-2-propenamide.