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

HRID 1526075Notes

Reaction equation

HRID 1526075 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-ba643b0707f8455fa725e3b259930542
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

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