Methanethiol → Tiaprofenic acid

HRID 1733646Notes

Reaction equation

HRID 1733646 reaction equation
CS[C:3]([C:9]1[S:10][C:11]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)([CH3:8])[C:4]([O:6]C)=[O:5].[Na].CS.O>CO>[C:14]([C:11]1[S:10][C:9]([CH:3]([CH3:8])[C:4]([OH:6])=[O:5])=[CH:13][CH:12]=1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962Water2×HCID 5360545SodiumHCID 12819460HCID 12819460, compound

Product 1

HCID 5468Tiaprofenic acidYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl α-methylthio-α-(5-benzoyl-2-thienyl)-propionate (320 mg) was dissolved in 1 ml of anhydrous methanol, and 1.0 ml (2.34 M) of a methanol solution of sodium salt of methyl mercaptan was added. The mixture was heated under reflux for 1 hour. In order to hydrolyze the ester, 1 ml of water was added and the mixture was heated under reflux for an additional 2 hours. After cooling, 20 ml of water was added, and the mixture was washed twice with 15 ml of methylene chloride. The aqueous layer was acidified to a pH of 1 with conc. hydrochloric acid, and extracted three times with 15 ml of methylene chloride. The organic layer was washed with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 176 mg of α-(5-benzoyl-2-thienyl)propionic acid in a yield of 68%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. additionwas added
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for an additional 2 hours
  6. temperatureAfter cooling
  7. washthe mixture was washed twice with 15 ml of methylene chloride
  8. extractionextracted three times with 15 ml of methylene chloride
  9. washThe organic layer was washed with 10 ml of water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3bd1154070f34b67a37f9baae087ce2d
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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