Thionyl Chloride → 2-Chloromethyl-3,4-dimethoxypyridinium chloride

HRID 1248307Notes

Reaction equation

HRID 1248307 reaction equation
O[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[ClH:15].[Cl:15][CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 107258093,4-Dimethoxy-2-pyridinemethanol

Product 1

HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Hydroxymethyl-3,4-dimethoxypyridine was reacted with thionyl chloride in chloroform to give 2-chloromethyl-3,4-dimethoxypyridine hydrochloride, m.p. 158°-9° (decomp), which was reacted with cysteamine hydrochloride and sodium ethoxide in ethanol to give 2-(3,4-dimethoxy-2-pyridylmethylthio)ethylamine.

Sources & evidence

ORD record
ord-a8e1fd03b7cc41c39e32fb98766add30
Source dataset
uspto-grants-1985_06
Patent number
US04523015

Reaction notes

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