Oxalyl chloride → 4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzoyl chloride

HRID 2307359Notes

Reaction equation

HRID 2307359 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)[N:3]=1.C(Cl)(=O)C([Cl:20])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([Cl:20])=[O:13])=[CH:10][CH:9]=2)[N:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6932064-(3,5-dimethyl-1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 128534534-(3,5-Dimethyl-1H-pyrazol-1-yl)benzoyl chlorideYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(3,5-dimethylpyrazol-1-yl)benzoic acid (1.34 g) in dichloromethane (25 ml) was added oxalyl chloride (1.0 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-(3,5-dimethylpyrazol-1-yl)benzoyl chloride (0.80 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-30757cb84d424d5cbce6da9a237cb0be
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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