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

HRID 2093546Notes

Reaction equation

HRID 2093546 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-5e5d6105d9ae4cd9a1f7844ae3e41eb7
Source dataset
uspto-grants-2013_05
Patent number
US08445504B2

Reaction notes

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