Dimethylformamide → 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

HRID 1748633Notes

Reaction equation

HRID 1748633 reaction equation
C(Cl)(=O)C(Cl)=O.C[N:8](C)[CH:9]=[O:10].[CH3:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:16]=[CH:15][C:14]=1C(O)=O>ClCCl.O>[CH3:12][C:13]1[N:17]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)[N:16]=[CH:15][C:14]=1[C:9]([NH2:8])=[O:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 107784295-methyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 178227615-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (3.8 ml) and N,N-dimethylformamide (catalytic amounts) were added at room temperature to a solution of 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acid (3.0 g) described in Reference Example 23 in dichloromethane (50 ml) and stirred at room temperature for two hours. The solvent and an excess amount of oxalyl chloride were evaporated, tetrahydrofuran (50 ml) was added to the residue, 28% aqueous ammonia was added under ice-cooling, and stirred at room temperature for two hours. After the reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The resulting organic layer was washed with 1N hydrochloric acid aqueous solution, 4N aqueous solution of sodium hydroxide, water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated to give 5-methyl-1-[4-(trifluoromethyl)phenyl]-1H-pyrazole-4-carboxamide (2.92 g) as a pale brown solid.

Workup

  1. customThe solvent and an excess amount of oxalyl chloride were evaporated
  2. additiontetrahydrofuran (50 ml) was added to the residue, 28% aqueous ammonia
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringstirred at room temperature for two hours
  6. customAfter the reaction
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer was washed with 1N hydrochloric acid aqueous solution, 4N aqueous solution of sodium hydroxide, water and saturated brine successively
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b94063d473de44b385e98b2f718fbb9c
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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