Thionyl Chloride → 3-(2-Chloroethoxy)pyridine hydrochloride

HRID 1737594Notes

Reaction equation

HRID 1737594 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 219089972-(Pyridin-3-yloxy)ethan-1-ol

Product 1

HCID 226249853-(2-Chloroethoxy)pyridine hydrochlorideYield 25.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (0.89 ml, 12 mmol) was added slowly to a solution of 3-(2-hydroxyethoxy)pyridine (1.13 g, 8 mmol) in trichloromethane (20 ml) at 5° C. The mixture was stirred at 5° C. for 1 hour and then at ambient temperature for 2 hours. The volatiles were removed by evaporation, the residue azeotroped with toluene and dried under vacuum to give 3-(2-chloroethoxy)pyridine hydrochloride (300 mg, 19%) as a solid.

Workup

  1. waitat ambient temperature for 2 hours
  2. customThe volatiles were removed by evaporation
  3. customthe residue azeotroped with toluene
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9c60a84ecc6e492b87729480888a391b
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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