Oxalyl chloride → 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

HRID 453073Notes

Reaction equation

HRID 453073 reaction equation
[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14](O)=[O:15])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)(=O)C([Cl:24])=O>CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([Cl:24])=[O:15])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 669392291-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 867619561-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flask, 1-(3,5-dichloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (0.40 g, 1.22 mmol), dichloromethane (10 mL) and oxalyl dichloride (0.31 g, 2.44 mmol) were added sequentially. After five drops of N,N-dimethyl formamide were added, a large amount of gas was released. After being stirred for 8 hours at room temperature, the reaction mixture was concentrated under reduced pressure. Then toluene (30 mL) was added, and was concentrated again under vacuum to give the product (0.42 g) as yellow solid in 100% yield.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThen toluene (30 mL) was added
  3. concentrationwas concentrated again under vacuum

Sources & evidence

ORD record
ord-9f39addc0d0145d89bdd7a063269e74d
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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