Dichloromethane → 1-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carbonyl chloride

HRID 453069Notes

Reaction equation

HRID 453069 reaction equation
[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14](O)=[O:15])=[CH:12][C:11]([CH3:17])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:18]CCl.C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([Cl:18])=[O:15])=[CH:12][C:11]([CH3:17])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 581589311-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 581589261-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL flask, 1-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid (0.37 g, 1.38 mmol), dichloromethane (10 mL) and oxalyl dichloride (0.35 g, 2.20 mmol) were added. After a drop of N,N-dimethyl formamide was added, a large number of gas was released. After being stirred for overnight at room temperature, the reaction mixture was concentrated under reduced pressure. Then 10 mL toluene was added, and the mixture was concentrated again under reduced pressure to give the product (0.40 g) as yellow oil in 100% yield.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThen 10 mL toluene was added
  3. concentrationthe mixture was concentrated again under reduced pressure

Sources & evidence

ORD record
ord-6cdea1f9f00c42fa8e8ed03df4727661
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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