Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine hydrochloride

HRID 2051773Notes

Reaction equation

HRID 2051773 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][N:4]=1.S(Cl)([Cl:12])=O>>[ClH:12].[Cl:12][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12325387(5-Methylpyridin-2-yl)methanol

Product 1

HCID 233137952-(Chloromethyl)-5-methylpyridine hydrochloride

Procedure

8.7 g of 2-hydroxymethyl-5-methyl-pyridine were added dropwise at a reaction temperature of 0°-10° to 18 ml of thionyl chloride. The reaction solution was next stirred for 15 hours at room temperature and then concentrated by evaporation on a rotary evaporator. The residue was treated with activated charcoal in alcohol and crystallised from alcohol-ether. 11.5 g of 2-chloromethyl-5-methylpyridine-hydrochloride having a m.p. 145°-146° was obtained.

Workup

  1. concentrationconcentrated by evaporation on a rotary evaporator
  2. additionThe residue was treated with activated charcoal in alcohol
  3. customcrystallised from alcohol-ether

Sources & evidence

ORD record
ord-5f09e803844141d1b5ee12439177dcd9
Source dataset
uspto-grants-1980_01
Patent number
US04182766

Reaction notes

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