Dimethylformamide → 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

HRID 890140Notes

Reaction equation

HRID 890140 reaction equation
[C:1]1([N:7]2[C:11]([C:12](O)=[O:13])=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:22])=O.CN(C)C=O>C(Cl)Cl.CN(C)C=O>[C:1]1([N:7]2[C:11]([C:12]([Cl:22])=[O:13])=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 222503231-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 222503331-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A sample of crude 1-phenyl-3-(trifluoromethyl)pyrazole-5-carboxylic acid (4.13 g, 16.1 mmol) was dissolved in methylene chloride (45 mL). The solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol), followed by N,N-dimethylformamide (0.010 mL, 0.13 mmol). Off-gassing began shortly after adding the N,N-dimethylformamide catalyst. The reaction mixture was stirred for ˜20 minutes under ambient conditions, then was heated to reflux for a period of 35 minutes. Volatiles were removed by stripping the reaction mixture on a rotary evaporator at a bath temperature of 55° C. The product consisted of 4.43 g of a light-yellow oil. The only impurity observed by 1H NMR was N,N-dimethylformamide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for a period of 35 minutes
  3. customVolatiles were removed
  4. customon a rotary evaporator at a bath temperature of 55° C

Sources & evidence

ORD record
ord-71b8113e3cb04113b0974e1f6ce1f413
Source dataset
uspto-grants-2006_02
Patent number
US06995178B2

Reaction notes

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