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

HRID 629461Notes

Reaction equation

HRID 629461 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C1COCC1>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 122143395-(chloromethyl)-2-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6-methylpyridin-3-yl)methanol (1.24 g) in THF (12.4 mL) was added thionyl chloride (1.10 mL) under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the obtained residue was suspended in ethyl acetate. The precipitate was collected by filtration, and washed with ethyl acetate-hexane to give the title compound (1.64 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-2f95570a6b704641abd4e40931c3ffec
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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