Hydrochloric Acid → Methyl 3,4-dimethoxy-5-sulfanylbenzoate

HRID 638951Notes

Reaction equation

HRID 638951 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([S:14]C(=O)N(C)C)[CH:5]=1.CO[Na].Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([SH:14])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86618872HCID 86618872, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68685859Methyl 3,4-dimethoxy-5-sulfanylbenzoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution 3-dimethylcarbamoylthio-4,5-dimethoxybenzoic acid methyl ester (800 mg, 2.67 mmol) in THF (21 mL) was added MeONa (0.5 M in MeOH, 21 mL) at room temperature and the reaction was heated to reflux. After refluxing for 3 h, the reaction mixture was cooled to room temperature, poured into 1 N HCl aqueous solution (150 mL) and extracted with mixture of EtOAc:hexane (1:1, 150 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-4,5-dimethoxybenzoic acid methyl ester (0.581 g).

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureAfter refluxing for 3 h
  3. extractionextracted with mixture of EtOAc:hexane (1:1, 150 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-035442844583498b8b1d253a6ff7b83b
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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