Thionyl Chloride → 1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carbonyl chloride

HRID 2067964Notes

Reaction equation

HRID 2067964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([Cl:19])=[O:16])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27771661-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 27761281-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carbonyl chlorideYield 100%

Procedure

A solution of 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid (1.5 g, 6.3 mmol) in thionyl chloride (18 mL) is warmed to reflux for 1 hour. After cooling to room temperature, the reaction mixture is concentrated in vacuo to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl chloride as a tan solid (1.6 g, 100%) which is used without further purification.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationthe reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-0e183f9d341449f69e8aa240dcb67ca9
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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