Oxalyl chloride → 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride

HRID 1507467Notes

Reaction equation

HRID 1507467 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:7]([C:8](O)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.C(Cl)(=O)C([Cl:17])=O>ClCCl.CN(C)C=O>[CH3:11][N:5]1[CH:6]=[C:7]([C:8]([Cl:17])=[O:9])[C:3]([C:2]([F:13])([F:12])[F:1])=[N:4]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27756651-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 27945811-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl chlorideYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 3-(Trifluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (3.00 g, 15.5 mmol) suspended in dichloromethane was added oxalyl chloride (2.24 g, 17.8 mmol) and dimethylformamide (one drop). The reaction mixture was stirred at room temperature until bubbling stopped at which point the organic solution was evaporated in vacuo to obtain 3.25 g (99%) of the title compound.

Workup

  1. customuntil bubbling
  2. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-ade4b3a28dc84f968c284811cea8ff43
Source dataset
uspto-grants-2015_12
Patent number
US09221814B2

Reaction notes

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