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

HRID 1292786노트

반응식

HRID 1292786 반응식
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]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178516151HCID 178516151, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dbae6f97299d4a45a17a542f9afd2206
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238689B2

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