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

HRID 453084Notes

Reaction equation

HRID 453084 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][N:11]=2)[N:3]=1.C(Cl)(=O)C([Cl:21])=O>CN(C)C=O.ClCCl>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([Cl:21])=[O:8])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][N:11]=2)[N:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 581589303-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 581589293-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 mL flask, 3-bromo-1-(3,5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid (0.4 g, 1.2 mmol), dichloromethane (10 mL) and oxalyl dichloride (0.31 g, 2.4 mmol) were added. After five drops of N,N-dimethyl formamide was added, a large number of gas was released. After being stirred for 8 hours at room temperature, the reaction mixture was evaporated to dryness at reduced pressure. Then toluene (100 mL) was added, and the reaction mixture was concentrated again under vacuum to give the product (0.42 g) as green solid in 100% yield.

Workup

  1. customthe reaction mixture was evaporated to dryness at reduced pressure
  2. additionThen toluene (100 mL) was added
  3. concentrationthe reaction mixture was concentrated again under vacuum

Sources & evidence

ORD record
ord-14505f5a164b4ab4bc8ed155a593d42e
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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