Oxalyl chloride → 4-(1H-pyrazol-1-yl)benzoyl chloride

HRID 1635845Notes

Reaction equation

HRID 1635845 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([Cl:18])=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 7365274-(1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 27764744-(1H-pyrazol-1-yl)benzoyl chlorideYield 93.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(pyrazol-1-yl)benzoic acid (1.56 g) in dichloromethane (25 ml) was added oxalyl chloride (1.04 g) and one drop of dimethylformamide. The mixture was stirred at room temperature for 18 hours to yield a clear solution. The volatile material was removed under reduced pressure to afford 4-(pyrazol-1-yl)benzoyl chloride as a pale yellow solid (1.58 g), which was utilized without further purification.

Workup

  1. customto yield a clear solution
  2. customThe volatile material was removed under reduced pressure

Sources & evidence

ORD record
ord-5df32dcdf3794072bd818d30b2d8360d
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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