Dimethylformamide → 5-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1822633Notes

Reaction equation

HRID 1822633 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][N:7]1[C:11](=O)[CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[NH:8]1.[OH-].[Na+].CN([CH:22]=[O:23])C>>[CH3:6][N:7]1[C:11]([Cl:3])=[C:10]([CH:22]=[O:23])[C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12386161-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol

Product 1

HCID 14784595-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeYield 77%

Conditions

Temperature
110 °C

Procedure

21.35 g of phosphorus oxychloride was dropwise added to 4.72 g of DMF at 10° C. or lower. After the temperature of the reaction solutio was returned to room temperature, the reaction mixture was stirred for 1 hour, and 10.71 g of 1-methyl-3-trifluoromethyl-5-pyrazolone was added thereto. The resulting mixture was heated up to 110° C., and stirred for 7 hours. After having been left to be at 70° C., the reaction mixture was poured into ice water. After pH of the mixture was made to be about 4 with an aqueous solution of sodium hydroxide added thereto, and precipitated crystals were taken out through filtration and dried to obtain 10.55 g of 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carbaldehyde.

Workup

  1. customwas returned to room temperature
  2. stirringstirred for 7 hours
  3. waitAfter having been left
  4. customto be at 70° C.
  5. additionadded
  6. customprecipitated crystals
  7. filtrationwere taken out through filtration
  8. customdried

Sources & evidence

ORD record
ord-e7e0e1e141d541cf8205c704f47aaba9
Source dataset
uspto-grants-2006_05
Patent number
US07037880B2

Reaction notes

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