Thionyl Chloride → 2-(2-Chloroethoxy)pyridine hydrochloride

HRID 279527Notes

Reaction equation

HRID 279527 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 122163042-(2-Hydroxyethoxy)pyridine

Product 1

HCID 226249922-(2-Chloroethoxy)pyridine hydrochlorideYield 132.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (0.55 ml, 7.55 mmol) was added to a solution of 2-(2-hydroxyethoxy)pyridine (700 mg, 5.04 mmol), (J. Org. Chem. 1977, 42, 1500), in trichloromethane (20 ml) at 5° C. The mixture was stirred for 1 hour at 5° C., allowed to warm to ambient temperature and stirred for a further 1 hour. The volatiles were removed by evaporation and by azeotroping with toluene to give 2-(2-chloroethoxy)pyridine hydrochloride (970 mg, 99%).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for a further 1 hour
  3. customThe volatiles were removed by evaporation
  4. customby azeotroping with toluene

Sources & evidence

ORD record
ord-badafdc1ec4347e8829bfb25b23e697e
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Reaction notes

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