Thionyl Chloride → 5,6-dichloropyridine-3-carbonyl Chloride

HRID 368288Notes

Reaction equation

HRID 368288 reaction equation
[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:14])=O>CN(C)C=O>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 27821565,6-dichloropyridine-3-carbonyl ChlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 5,6-dichloronicotinic acid (5.2 g, 27 mmol) in thionyl chloride (50 mL) containing dimethylformamide (2 drops) was heated under reflux conditions for two hours; cooled and concentrated under reduced pressure to afford 5,6-dichloronicotinoyl chloride (5.6 g, 99%) as a yellow oil.

Workup

  1. temperaturewas heated under reflux conditions for two hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ac7b5632e2f4aee8b3c0e6b1a583c55
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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