Thionyl Chloride → 3-Chloro-2-(chloromethyl)-4-methoxy-5-methylpyridine hydrochloride

HRID 81696Notes

Reaction equation

HRID 81696 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11]O)=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9].S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:3]([CH2:11][Cl:15])=[N:4][CH:5]=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58201206HCID 58201206, compound

Product 1

HCID 666179323-Chloro-2-(chloromethyl)-4-methoxy-5-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The above (3-chloro-4-methoxy-5-methylpyridin-2-yl)methanol (530 mg) was dissolved in 20 ml of chloroform, and thionyl chloride (1.03 ml) was then added dropwise to the solution under cooling on ice. The resulting mixture was stirred at room temperature for 3 hours. Thereafter, the reaction solution was concentrated, and it was then washed with a mixed solvent of ether-hexane, so as to obtain the title compound (410 mg) as a solid.

Workup

  1. temperatureunder cooling on ice
  2. concentrationThereafter, the reaction solution was concentrated
  3. washit was then washed with a mixed solvent of ether-hexane

Sources & evidence

ORD record
ord-348dac1f4bee4d81bc75fc2c5f0979fd
Source dataset
uspto-grants-2014_09
Patent number
US08846703B2

Reaction notes

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