Thionyl Chloride → 4,5,6-Trichloropicolinoyl chloride

HRID 1837440Notes

Reaction equation

HRID 1837440 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([OH:12])=O)[CH:3]=1.S(Cl)([Cl:15])=O>ClC(Cl)C>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([Cl:15])=[O:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 129936922-Pyridinecarboxylic acid, 4,5,6-trichloro-

Product 1

HCID 129936934,5,6-Trichloropicolinoyl chloride

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 4,5,6-trichloropyridine-2-carboxylic acid (5.20 g, 23.1 mmol) and thionyl chloride (3.0 mL) in dichloroethane (30 mL) was refluxed until the evolved gas ceased. The reaction mixture was concentrated to give 4,5,6-trichloropyridine-2-carbonyl chloride (5.60 g, 23.0 mmol), mp 60-62° C.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d44e9346ba8e4160826637104e603b28
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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