Thionyl Chloride → 4-(Chloromethyl)pyridinium chloride

HRID 1389234Notes

Reaction equation

HRID 1389234 reaction equation
[ClH:1].O[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.S(Cl)([Cl:12])=O>C1C=CC=CC=1>[ClH:12].[Cl:1][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1222843762302-28-7

Product 1

HCID 745704-(Chloromethyl)pyridinium chlorideYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 37.0 g (0.25 mole) of 4-hydroxymethylpyridine hydrochloride and 150 ml of thionyl chloride is heated under reflux for 2 hours. After cooling, 250 ml of benzene are added to the reaction mixture, followed by filtering and washing the precipitate with benzene. There are obtained 32.0 g of 4-chloromethylpyridine hydrochloride (76% of theory); m.p. 171-172° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationby filtering
  5. washwashing the precipitate with benzene

Sources & evidence

ORD record
ord-9b799644c50347cfbf584b490d63e12c
Source dataset
uspto-grants-1981_01
Patent number
US04243807

Reaction notes

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