Phosphorus pentachloride → phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate
Reaction equation
[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][C:2](=[CH:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3](=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[S:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Toluene (4 mL) was added to a mixture of 2-methyl-N-phenyl-3-(phenylthio)acrylamide (0.80 g) and phosphorus pentachloride (0.62 g), and the mixture was stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure. To the concentrate was added DMF (35 mL), and then, phenylmercaptan sodium salt (793 mg) was added portionwise thereto. The mixture was stirred at room temperature for 2 hours. To the reaction mixture was added tert-butyl methyl ether, and then a 1 N aqueous sodium hydroxide solution was added, thereby the solution was separated. The organic layer was washed with water three times, dried and then concentrated. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain phenyl 2-methyl-N-phenyl-3-(phenylthio)thioacrylimidate (0.4 g).