Thionyl Chloride → 4-Chloro-2-(chloromethyl)pyridine--hydrogen chloride (1/1)

HRID 2086256Notes

Reaction equation

HRID 2086256 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.S(Cl)([Cl:12])=O>CN(C=O)C.C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Cl:12])[CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2763167(4-Chloropyridin-2-yl)methanol

Product 1

HCID 227272744-Chloro-2-(chloromethyl)pyridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 4-chloro-2-hydroxymethylpyridine (430 mg), thionyl chloride (0.43 ml) and DMF (1 drop) in chloroform (20 ml) was heated under reflux for 2 hours. The reaction mixture was concentrated to obtain the title compound (0.44 g) as a tan powder.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3531d839c3e14f35a2bd80a678c857fc
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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