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

HRID 1384645

Reaktionsgleichung

Reaktionsgleichung von HRID 1384645
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 226249853-(2-Chloroethoxy)pyridine hydrochlorideAusbeute 25,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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. 1H NMR Spectrum: (DMSOd6) 3.99(t, 2H); 4.42(t, 2H); 7.82(dd, 1H); 8.05(dd, 1H); 8.42(d, 1H); 8.62(s, 1H)

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-aab8ae36889b4383ae6c0a660de451db
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258951B1

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