Methanol → Methyl 2-((phenylcarbonothioyl)thio)acetate

HRID 1039165Notes

Reaction equation

HRID 1039165 reaction equation
[C:1]([S:9][CH2:10][C:11]([OH:13])=[O:12])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:12][C:11](=[O:13])[CH2:10][S:9][C:1](=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 70336((Phenylthioxomethyl)thio)acetic acid

Product 1

HCID 71356278Methyl 2-((phenylcarbonothioyl)thio)acetateYield 97%

Procedure

Add a solution of thiobenzoylsulfanylacetic acid (5.5 g, 26.0 mmol) in methanol (100 mL) and to a solution of thionyl chloride (52 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, dissolve the residue in ethyl acetate (200 mL), wash with saturated NaHCO3 (200 mL) and brine (200 mL) solutions, and dry over sodium sulfate. Remove the solvent under reduced pressure to provide thiobenzoylsulfanylacetic acid methyl ester (5.7 g, 97%).

Workup

  1. temperatureat reflux for 12 hours
  2. customRemove the solvent under reduced pressure
  3. dissolutiondissolve the residue in ethyl acetate (200 mL)
  4. washwash with saturated NaHCO3 (200 mL) and brine (200 mL) solutions
  5. dry with materialdry over sodium sulfate
  6. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-688984c870574770a6a80db22151b732
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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