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

HRID 78725

Reaction equation

HRID 78725 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]=1

Participants

4

Reactant 3

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

Product 1

HCID 71356278Methyl 2-((phenylcarbonothioyl)thio)acetateYield 98%

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%).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated in vacuo and ethyl acetate
  3. additionwas added
  4. washThe mixture was washed with sat. aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d3aef15bfca74418ab7803638a34a11d
Source dataset
uspto-grants-2014_09
Patent number
US08841449B2

Linked notes

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