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

HRID 1384542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384542
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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]+

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0d8bf44d60bf4798bb37099cc7166823
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258951B1

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