Oxalyl chloride → HCID 22605448, compound

HRID 2307355Notes

Reaction equation

HRID 2307355 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[N:3]=1.C(Cl)(=O)C([Cl:19])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([Cl:19])=[O:12])=[CH:9][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 11804784-(3-methyl-1H-pyrazol-1-yl)benzoic acid

Product 1

HCID 22605448HCID 22605448, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(3-methylpyrazol-1-yl)benzoic acid (1.84 g) in dichloromethane (25 ml) was added oxalyl chloride (1.16 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. Dichloromethane was added, the solution filtered, and the solvent evaporated under reduced pressure to yield 4-(3-methylpyrazol-1-yl)benzoyl chloride as a yellow oil (1.76 g), which was utilized without further purification.

Workup

  1. customthe volatile material was removed under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe solution filtered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-db75684c8e3041db91d856ed3152b439
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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