Dimethylformamide → Methyl 2-methyl-3-(methylthio)benzoate

HRID 906121Notes

Reaction equation

HRID 906121 reaction equation
[SH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC.CN(C)[CH:22]=[O:23]>C(OCC)(=O)C>[CH3:11][C:3]1[C:2]([S:1][CH3:12])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:23][CH3:22])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 109318223-Mercapto-2-methylbenzoic acid

Product 1

HCID 67404114Methyl 2-methyl-3-(methylthio)benzoateYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-mercapto-2-methylbenzoic acid (180 mg, 1.05 mmol), cesium carbonate (690 mg, 2.1 mmol) and iodomethane (132 L1, 2.10 mmol) in dimethylformamide (3 mL) was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate then washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, and brine then dried over anhydrous sodium sulfate. Filtration and concentration afforded 138 mg, 0.62 mmol (58%) of methyl 2-methyl-3-(methylthio)benzoate. 1H NMR (400 MHz, CDCl3): 7.58 (d, 1H), 7.41 (d, 1H), 7.21-7.16 (m, 1H), 4.09 (s, 3H), 2.83 (s, 3H), 2.58 (s, 3H). MS (EI) for C10H12SO2: 197 (MH+).

Workup

  1. washthen washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, and brine
  2. dry with materialthen dried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2e578a4f7d32431ba5db9e59042f0008
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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