Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

HRID 889295Notes

Reaction equation

HRID 889295 reaction equation
O[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:12])=O>>[Cl:12][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

Procedure

1.00 g (8.12 mmol) 3-(hydroxymethyl)-2-methylpyridine are initially introduced into the reaction vessel and 5.9 ml (81.2 mmol) thionyl chloride are slowly added at 0° C. The mixture is stirred under reflux for 3 h. It is concentrated, saturated sodium bicarbonate solution is added to the residue and the mixture is extracted several times with diethyl ether. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated.

Workup

  1. additionare slowly added at 0° C
  2. temperatureunder reflux for 3 h
  3. concentrationIt is concentrated
  4. additionsaturated sodium bicarbonate solution is added to the residue
  5. extractionthe mixture is extracted several times with diethyl ether
  6. washThe combined organic phases are washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a6efac4c304a4666ad175b266361c7ac
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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