Dimethylformamide → Methyl 3-(methylthio)benzoate

HRID 732020

Reaction equation

HRID 732020 reaction equation
[CH3:1]I.[SH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)C(O)=O.[C:13](=[O:16])([O-])[O-].[K+].[K+].CN([CH:22]=[O:23])C>C(OCC)(=O)C>[CH3:13][O:16][C:22](=[O:23])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([S:3][CH3:1])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 6432769Methyl 3-(methylthio)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (0.972 mL) was added to a mixture of 3-mercapto-benzoic acid (601 mg, 3.9 mmol) and potassium carbonate (2.7 g, 19.5 mmol) in DMF (8 mL) in an ice-bath. After the reaction was warmed to room temperature and stirred for 1 hour, the reaction mixture was diluted with ethyl acetate, washed with water (3×), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3-methylsulfanyl-benzoic acid methyl ester (684 mg, 96%, yellow oil). 1H NMR (CDCl3), δ (ppm): 7.90 (s, 1H), 7.80 (d, 1H), 7.44 (d, 1H), 7.35 (t, 1H), 3.92 (s, 3H), 2.53 (s, 3H).

Workup

  1. washwashed with water (3×)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d87b92137e284755b19f313db238c86a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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