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

HRID 453080Notes

Reaction equation

HRID 453080 reaction equation
[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14](O)=[O:15])=[CH:12][C:11]([O:17][CH2:18][C:19]#[CH:20])=[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]([O:17][CH2:18][C:19]#[CH:20])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 581589381-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 581589231-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-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-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylic acid (0.2 g, 0.64 mmol), dichloromethane (10 mL) and oxalyl dichloride (0.16 g, 1.2 mmol) were added. After five drops of N,N-dimethyl formamide were 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 100 mL toluene was added, and the reaction mixture was concentrated again under reduced pressure to give the product (0.21 g) as yellow solid in 100% yield.

Workup

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

Sources & evidence

ORD record
ord-4241e53d751f42e5b5856a35243fbbd8
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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