Hydrochloric Acid → Methyl 3-methoxy-5-sulfanylbenzoate

HRID 638942Notes

Reaction equation

HRID 638942 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([S:12]C(=O)N(C)C)[CH:5]=1.CO[Na].Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([SH:12])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86618870HCID 86618870, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68686673Methyl 3-methoxy-5-sulfanylbenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-dimethylcarbamylthio-5-methoxybenzoic acid methyl ester (500 mg, 1.86 mmol) in THF (10 mL) at room temperature was added MeONa (0.5 M in MeOH, 10.0 mL, 5.0 mmol, 2.69 eq.). The reaction was refluxed for 2 h, then cooled to room temperature and added to 1.0 N HCl aqueous solution (150 mL). The resulting mixture was extracted with EtOAc/hexanes (1:1, 150 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo to give 3-mercapto-5-methoxybenzoic acid methyl ester (0.365 g). The product was used without further purification.

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. extractionThe resulting mixture was extracted with EtOAc/hexanes (1:1, 150 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a6fb25a094740a0998572628d8d55dd
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

Loading…