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

HRID 23468

反応式

HRID 23468 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f6d26795c6541b69470d018a06604b9
出典データセット
uspto-grants-2005_02
特許番号
US06852711B2

関連ノート

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