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

HRID 23468

반응식

HRID 23468 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6f6d26795c6541b69470d018a06604b9
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852711B2

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