Dimethylformamide → 5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1172093ノート

反応式

HRID 1172093 の反応式
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[C:11]1([N:17]2[C:21](O)=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[Cl:3][C:21]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:20]=1[CH:8]=[O:9]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178516151HCID 178516151、化合物

生成物 1

HCID 14790525-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde収率 79.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

33.6 g (219.1 mmoles) of phosphorus oxychloride was added to 7.7 g (105.2 mmoles) of N,N-dimethylformamide with ice-cooling. Thereto was added, at room temperature, 20 g (87.7 mmoles) of 1-phenyl-3-trifluoromethyl-1H-pyrazol-5-ol. The resulting mixture was refluxed for 1 hour with heating, to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water with ice-cooling, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 19.1 g (yield: 79.1%) of 5-chloro-1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde as white crystals.

後処理

  1. temperaturecooling
  2. additionThereto was added, at room temperature
  3. temperatureThe resulting mixture was refluxed for 1 hour
  4. temperaturewith heating
  5. customto give rise
  6. customto a reaction
  7. customAfter the completion of the reaction
  8. temperaturecooling
  9. extractionfollowed by extraction with chloroform
  10. washThe resulting organic layer was washed with an aqueous sodium hydrogencarbonate solution
  11. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  12. distillationThe resulting solution was subjected to vacuum distillation
  13. customto remove the solvent
  14. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

出典と根拠

ORDレコード
ord-6a9c8970342d4d8ebb7b1b1d6e9de1a4
出典データセット
uspto-grants-2010_11
特許番号
US07833939B2

反応ノート

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