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

HRID 516500Notes

Reaction equation

HRID 516500 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 acid2×

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 (i.e. the product of Step B) (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-8d36ab973e2a4d97ad37baa5fefb71d5
Source dataset
uspto-grants-2015_08
Patent number
US09113630B2

Reaction notes

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