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Oxalyl chloride → 4-(3,5-Dimethylpyrazol-1-yl)benzoyl chloride

HRID 1635851
Notes
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Reaction equation

HRID 1635851 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

HCID 128534534-(3,5-Dimethylpyrazol-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-716a29b4c8644d149d8b3b1dc57f0d61
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06511974B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes