Thionyl Chloride → 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl Chloride

HRID 251909

Reaction equation

HRID 251909 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13](O)=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:22])=O>>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([Cl:22])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl Chloride

Procedure

A mixture of 16.08 g of 1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid and 12 ml of thionyl chloride was heated to reflux for 2 hours. The reaction mixture was allowed to cool to room temperature and subjected to distillation under reduced pressure (125° C./3 mmHg) to obtain 14.2 g of 1-(3-chloro-2-pyridinyl)-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride of the formula:

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. distillationsubjected to distillation under reduced pressure (125° C./3 mmHg)

Sources & evidence

ORD record
ord-bdf1f31ffb054b71bf3e8b5593f87977
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Linked notes

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