Thionyl Chloride → 3-Chloro-5-trifluoromethyl-pyridine-2-carbonyl chloride

HRID 650478

Reaction equation

HRID 650478 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([OH:14])=O)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[C:3]([C:12]([Cl:17])=[O:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 28219083-Chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid

Product 1

HCID 220135553-Chloro-5-trifluoromethyl-pyridine-2-carbonyl chloride

Conditions

Temperature
25 °C

Procedure

89.3 g of 3-chloro-5-trifluoromethyl-2-pyridinecarboxylic acid (Example P3) are slowly heated to reflux with 60 ml of thionyl chloride and the mixture is then stirred at that temperature for 4 hours, after which it is cooled to 25° C. and concentrated to dryness in vacuo. Twice, toluene is added and the mixture is again concentrated to dryness. 94.0 g of the desired product are obtained in the form of a yellow residue.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. additionTwice, toluene is added
  3. concentrationthe mixture is again concentrated to dryness

Sources & evidence

ORD record
ord-ad87a9bcb6d84ff58a1cd54544b1e42f
Source dataset
uspto-grants-2001_08
Patent number
US06274536B1

Linked notes

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