Thionyl Chloride → 2-(2-Chloroethoxy)pyridine hydrochloride
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperatureto warm to ambient temperature
- stirringstirred for a further 1 hour
- customThe volatiles were removed by evaporation
- customby azeotroping with toluene
Sources & evidence
- ORD record
- ord-d2cd370254ed442996ecb4665cb0b68b
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962458
Reaction notes
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