Oxalyl chloride → (Pyridin-3-yl)-1H-pyrazole-4-carbonyl chloride hydrochloride

HRID 43035Notes

Reaction equation

HRID 43035 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[N:8]2)[CH:2]=1.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[ClH:18].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]([Cl:18])=[O:14])[CH:9]=[N:8]2)[CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 545930711-(Pyridin-3-yl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 86762039(Pyridin-3-yl)-1H-pyrazole-4-carbonyl chloride hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4.00 g (21.15 mmol) of 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylic acid were initially charged in approx. 100 ml of dichloromethane, and admixed with 2 drops of dimethylformamide under argon. 7.783 g (61.32 mmol) of oxalyl chloride were added dropwise and, after the end of the addition, the mixture was stirred at room temperature for 1 hour. The solution was concentrated, and the residue was admixed with approx. 10 ml of toluene and concentrated. This gave a colourless solid which was converted further immediately.

Workup

  1. additionafter the end of the addition
  2. concentrationThe solution was concentrated
  3. concentrationconcentrated
  4. customThis gave a colourless solid which

Sources & evidence

ORD record
ord-a3b7ca1d85304d2d989e3ef239939877
Source dataset
uspto-grants-2013_09
Patent number
US08536204B2

Reaction notes

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