Thionyl Chloride → 6-Chloromethyl-2-methylpyridinium chloride

HRID 2424890Notes

Reaction equation

HRID 2424890 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1.S(Cl)([Cl:12])=O>>[ClH:12].[Cl:12][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 765456-Chloromethyl-2-methylpyridinium chloride

Procedure

2-(Hydroxymethyl)-6-methylpyridine (3.7 g, 29.4 mmol) was added portion wise at 0° C. to thionylchloride (35 mL, 477 mmol). The reaction mixture was then stirred at room temperature for 18 h. Excess thionylchloride was removed under vacuum and the crude 2-chloromethyl-6-methyl-pyridine hydrochloride (5.1 g, light brown solid) was used without any further purification.

Workup

  1. customExcess thionylchloride was removed under vacuum
  2. customthe crude 2-chloromethyl-6-methyl-pyridine hydrochloride (5.1 g, light brown solid) was used without any further purification

Sources & evidence

ORD record
ord-72280db26e3140959f303ee03f2e058e
Source dataset
uspto-grants-2011_06
Patent number
US07964620B2

Reaction notes

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