Cesium carbonate → 3-Tert-butyl-4-dimethylthiocarbamoyloxy-benzoic acid methyl ester

HRID 23468

Reaction equation

HRID 23468 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][N:23]([CH3:27])[C:24](Cl)=[S:25]>C(#N)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:24](=[S:25])[N:23]([CH3:27])[CH3:22])=[C:6]([C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27871Dimethylthiocarbamoyl chlorideHCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

Product 1

HCID 542971683-Tert-butyl-4-dimethylthiocarbamoyloxy-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.0 g (14.4 mmol) of 3-tert-butyl-4-hydroxy-benzoic acid methyl ester (Aust. J. Chem., 1978;31:907-916), cesium carbonate (7.04 g, 21.6 mmol), and acetonitrile (50 mL) was heated to reflux and then treated with N,N-dimethylthiocarbamoyl chloride (2.67 g, 21.6 mmol) all at once. The mixture was refluxed for 2 hours, cooled to room temperature, and quenched with 1N HCl. The solution was extracted with EtOAc; the organic layer was washed with 1N NaOH and brine, dried (MgSO4), and concentrated. The residue was chromatographed over silica gel, eluting with 3:2 hexane:EtOAc, to give 3-tert-butyl-4-dimethylthiocarbamoyloxy-benzoic acid methyl ester.

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was refluxed for 2 hours
  3. customquenched with 1N HCl
  4. extractionThe solution was extracted with EtOAc
  5. washthe organic layer was washed with 1N NaOH and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel
  9. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-6f6d26795c6541b69470d018a06604b9
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Linked notes

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