Ethanol → 4-Chloro-2-chloromethyl-3,5-dimethylpyridinium chloride

HRID 1819271Notes

Reaction equation

HRID 1819271 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH2:9]O)[C:3]=1[CH3:11].CN(C=O)C.S(Cl)([Cl:19])=O.C(O)C>C1(C)C=CC=CC=1>[Cl-:1].[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][NH+:5]=[C:4]([CH2:9][Cl:19])[C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 9795246(4-Chloro-3,5-dimethylpyridin-2-YL)methanol

Product 1

HCID 685397504-Chloro-2-chloromethyl-3,5-dimethylpyridinium chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-chloro-2-hydroxymethyl-3,5-dimethylpyridine (60.7 g, 354 mmol) and DMF (0.25 mL, 3.54 mmol) in toluene (200 mL) was added thionyl chloride (26.9 mL, 371 mmol) over 2 h at 15-30° C. After stirring for 2 more h at ambient temperature, ethanol (6 mL) was added to the thick slurry. The solids were filtered off at about 10° C., washed with toluene (80 mL) and dried at 40° C. in vacuo to give 4-chloro-2-chloromethyl-3,5-dimethylpyridinium chloride as an off-white solid (m. p. 195-196° C.); yield 66.5 g (84%).

Workup

  1. filtrationThe solids were filtered off at about 10° C.
  2. washwashed with toluene (80 mL)
  3. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-151d3854aefa45b982e22f6bcd61b1c8
Source dataset
uspto-grants-2009_10
Patent number
US07601737B2

Reaction notes

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