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

HRID 882980Notes

Reaction equation

HRID 882980 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-41df0f954d0a441498005ea1e1d3eba0
Source dataset
uspto-grants-2012_08
Patent number
US08236813B2

Reaction notes

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