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

HRID 1635849Notes

Reaction equation

HRID 1635849 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH:6]=1.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([Cl:19])=[O:12])=[CH:9][CH:8]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 226054604-(4-methyl-1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 226054414-(4-Methyl-1H-pyrazol-1-yl)benzoyl chlorideYield 94.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(4-methylpyrazol-1-yl)benzoic acid (0.75 g) in dichloromethane (15 ml) was added oxalyl chloride (0.50 g) and one drop of dimethylformamide. The mixture was stirred at room temperature for 18 hours and the volatile material was removed under reduced pressure. The residue was dissolved in hexane and filtered through diatomaceous earth. Evaporation of the solvent in vacuo yielded 4-(4-methylpyrazol-1-yl)benzoyl chloride (0.77 g), which was used without further purification.

Workup

  1. customthe volatile material was removed under reduced pressure
  2. dissolutionThe residue was dissolved in hexane
  3. filtrationfiltered through diatomaceous earth
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-86bb837937164544a98e7b24f30adcf1
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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