Thionyl Chloride → 2-Chloro-3-(chloromethyl)-5-methylpyridine

HRID 413476Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[Cl:1][C:2]1[C:7]([CH2:8][Cl:13])=[CH:6][C:5]([CH3:10])=[CH:4][N:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 12056721(2-Chloro-5-methylpyridin-3-yl)methanol

Product 1

HCID 112060822-Chloro-3-(chloromethyl)-5-methylpyridine

Procedure

comprising reacting 2-chloro-3-hydroxymethyl-5-methylpyridine with thionyl chloride to give 2-chloro-3-chloromethyl-5-methylpyridine, followed by reacting the 2-chloro-3-chloromethyl-5-methylpyridine thus obtained with 2-nitroimino-1,3-diazacyclopentane in the presence of a base and an organic solvent, to give 1-(2-chloro-5-methyl-3-pyridylmethyl)-2-nitroiminoimidazolidine.

Sources & evidence

ORD record: ord-ba8a223b92544fb29e02e2c44799e391
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06566528B1

Reaction notes

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