Thionyl Chloride → 2-Chloro-4-(chloromethyl)-6-methoxypyridine hydrochloride

HRID 1384617Notes

Reaction equation

HRID 1384617 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12]O)[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1>C1(C)C=CC=CC=1>[ClH:3].[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][Cl:3])[CH:9]=[C:8]([O:14][CH3:15])[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11457961(2-Chloro-6-methoxypyridin-4-yl)methanol

Product 1

HCID 226250592-Chloro-4-(chloromethyl)-6-methoxypyridine hydrochlorideYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.0 ml) was added to a solution of 2-chloro-4-hydroxymethyl-6-methoxypyridine (0.9 g, 5.2 mmol) in toluene 10 ml) and the mixture stirred at ambient temperature for 1 hour. The volatiles were removed by evaporation, the residue was azeotroped with toluene and dried under vacuum to give 2-chloro-4-chloromethyl-6-methoxypyridine hydrochloride (0.88 g, 74%). 1H NMR Spectrum: (DMSOd6) 3.85(s, 3H); 4.70(s, 2H); 6.90(s, 1H); 7.15(s, 1H)

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was azeotroped with toluene
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f61b79e1cae54c609715831329eb3332
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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