Thionyl Chloride → 4-Chloro-2-chloromethyl-3-methoxypyridine chloride

HRID 1816672Notes

Reaction equation

HRID 1816672 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[C:3]=1[O:10][CH3:11].S(Cl)([Cl:14])=O>C(Cl)Cl>[Cl-:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Cl:14])[C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11480736(4-Chloro-3-methoxypyridin-2-yl)methanol

Product 1

HCID 224936324-Chloro-2-chloromethyl-3-methoxypyridine chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-2-hydroxymethyl-3-methoxypyridine (41.0 g) was dissolved in methylene chloride (150 mL), and thionyl chloride was added dropwise over 10 minutes with stirring under cooling with an ice bath. The ice bath was removed, and the mixture was stirred for 30 minutes at room temperature. The solvent was removed under reduced pressure, and hexane (50 mL) was added to the residue, followed by distillation, whereby 4-chloro-2-chloromethyl-3-methoxypyridine chloride was obtained as a brown solid (54.1 g, yield: quantitative).

Workup

  1. temperatureunder cooling with an ice bath
  2. customThe ice bath was removed
  3. stirringthe mixture was stirred for 30 minutes at room temperature
  4. customThe solvent was removed under reduced pressure, and hexane (50 mL)
  5. additionwas added to the residue
  6. distillationfollowed by distillation

Sources & evidence

ORD record
ord-d65f7d6fd2ee4c2682ece78419a10519
Source dataset
uspto-grants-2005_04
Patent number
US06884810B2

Reaction notes

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