HCID 86618868, compound → Methyl 4-methoxy-3-sulfanylbenzoate

HRID 638938Notes

Reaction equation

HRID 638938 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([S:12]C(=O)N(C)C)[CH:5]=1.CO[Na]>C1COCC1.Cl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([SH:12])[CH:5]=1

Participants

5

Reactant 2

HCID 86618868HCID 86618868, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68685155Methyl 4-methoxy-3-sulfanylbenzoateYield 107.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-dimethylcarbamoylthio-4-methoxybenzoic acid methyl ester (530 mg, 1.97 mmol) in THF (10 mL), was added MeONa (10 mL, 0.5 M solution in MeOH). The resulting mixture was heated to reflux for 3 h and then cooled to room temperature. The reaction mixture was diluted with 1N HCl aqueous solution (100 mL), extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo to afford 3-mercapto-4-methoxybenzoic acid methyl ester (0.42 g). The product was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layer was washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3fea8d97b6c4c4689b45ae49430c2e2
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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