Methyl iodide → HCID 86618869, compound

HRID 638941Notes

Reaction equation

HRID 638941 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][C:12](=[S:16])[N:13]([CH3:15])[CH3:14])[CH:5]=1.[C:18]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH3:18])[CH:7]=[C:6]([O:11][C:12](=[S:16])[N:13]([CH3:14])[CH3:15])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21364997HCID 21364997, compound

Product 1

HCID 86618869HCID 86618869, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-dimethylthiocarbamyloxy-5-hydroxybenzoic acid methyl ester (2.37 g, impure) in DMF (30 mL) at room temperature was added K2CO3 (3.85 g, 27.9 mmol), followed by iodomethane (1.16 mL, 18.6 mmol). After stirring for 3.5 h at room temperature the reaction mixture was partitioned between ethyl ether (200 mL) and H2O (200 mL). The organic layer was washed with brine (100 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 33% EtOAc in hexanes as an eluent to furnish 3-dimethylthiocarbamyloxy-5-methoxybenzoic acid methyl ester (1.30 g, 4.83 mmol).

Workup

  1. customwas partitioned between ethyl ether (200 mL) and H2O (200 mL)
  2. washThe organic layer was washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel using 33% EtOAc in hexanes as an eluent

Sources & evidence

ORD record
ord-ac511a3beba84001a224ffb20f39f715
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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