Thionyl Chloride → 4-(2-Chloroethoxy)pyridine hydrochloride

HRID 1384542Notes

Reaction equation

HRID 1384542 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 33760122-(Pyridin-4-yloxy)ethanol

Product 1

HCID 226249204-(2-Chloroethoxy)pyridine hydrochlorideYield 134%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (0.75 ml, 10 mmol) was added to a solution of 4-(2-hydroxyethoxy)pyridine (0.9 g, 6.5 mmol), (J. Chem. Soc. Perkin II, 1987, 1867), 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 2 hours. The volatiles were removed by evaporation and by azeotroping with toluene to give 4-(2-chloroethoxy)pyridine hydrochloride (1.3 g, 100%). 1H NMR Spectrum: (DMSOd6) 4.03(t, 2H); 4.62(t, 2H); 7.58(d, 2H); 8.77(d, 2H) MS-ESI: 158 [MH]+

Workup

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

Sources & evidence

ORD record
ord-0d8bf44d60bf4798bb37099cc7166823
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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