Dimethylformamide → HCID 19080746, compound

HRID 254222Notes

Reaction equation

HRID 254222 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[CH2:11]([N:13]1[C:17](O)=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[N:14]1)[CH3:12]>O>[Cl:3][C:17]1[N:13]([CH2:11][CH3:12])[N:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:16]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178463141HCID 178463141, compound

Product 1

HCID 19080746HCID 19080746, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

91.1 g (591.2 mmoles) of phosphorus oxychloride was added to 18.0 g (246.3 mmoles) of N,N-dimethylformamide with ice-cooling. Thereto was added, at room temperature, 35.5 g (197.1 mmoles) of 1-ethyl-3-trifluoromethyl-1H-pyrazol-5-ol. The mixture was heated and refluxed for 3 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water with ice-cooling, and extraction with chloroform was conducted. 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 reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain a crude product of 5-chloro-1-ethyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde.

Workup

  1. temperaturecooling
  2. additionThereto was added, at room temperature
  3. temperatureThe mixture was heated
  4. temperaturerefluxed for 3 hours
  5. customto give rise
  6. customto a reaction
  7. customAfter the completion of the reaction
  8. temperaturecooling
  9. extractionextraction 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 reduced pressure distillation
  13. customto remove the solvent
  14. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c2249ff81b834cec9d9ed032421b8cc8
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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