Methanol → Methyl 2-((phenylcarbonothioyl)thio)acetate
Reaction equation
[C:1]1([C:7]([S:9][CH2:10][C:11]([OH:13])=[O:12])=[S:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:18]O>>[C:1]1([C:7]([S:9][CH2:10][C:11]([O:13][CH3:18])=[O:12])=[S:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Procedure
2-((Phenylcarbonothioyl)thio)acetic acid (10 g, 47.1 mmol) was dissolved in 200 mL of methanol followed by the dropwise addition of thionylchloride (16 g, 120 mmol) at room temperature. The reaction mixture was refluxed for 4 hours. The reaction mixture was concentrated in vacuo and ethyl acetate was added. The mixture was washed with sat. aq. NaHCO3 and brine and dried over Na2SO4. The reaction mixture was concentrated in vacuo to afford Methyl 2-((phenylcarbonothioyl)thio)acetate 2 as brown oil (10.5 g, 98%).