Thionyl Chloride → 2-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

HRID 251918Notes

Reaction equation

HRID 251918 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13](O)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1.S(Cl)([Cl:22])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([Cl:22])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 179605961-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 574582382-(2-Chloro-phenyl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl chloride

Procedure

A mixture of 10.65 g of 1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid and 8 ml of thionyl chloride heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature, concentrated under reduced pressure, and subjected to distillation under reduced pressure (110° C./5 mmHg) to obtain 8.39 g of 1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride of the formula:

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. distillationsubjected to distillation under reduced pressure (110° C./5 mmHg)

Sources & evidence

ORD record
ord-5bab78e580ed45aca7023d8169ff2609
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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