Thionyl Chloride → 2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine

HRID 357557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 357557
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 104657494-(3-Methoxypropoxy)-3-methyl-2-pyridinemethanol

Produkt 1

HCID 110316672-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridineAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

450 mg of the 2-hydroxymethyl-4-(3-methoxypropoxy)-3-methylpyridine prepared above was dissolved in 20 ml of dichloromethane to obtain a solution. 760 mg of thionyl chloride was dropwise added to this solution at 0° C. The obtained mixture was stirred at a room temperature for 2 hours. After the completion of the reaction, the reaction mixture was distilled to remove the dichloromethane and the thionyl chloride. A saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue. The obtained mixture was extracted with chloroform. The obtained chloroform layer was concentrated to obtain 470 mg of 2-chloromethyl-4-(3-methoxypropoxy)-3-methylpyridine as a brown crystal.

Aufarbeitung

  1. customto obtain a solution
  2. customAfter the completion of the reaction
  3. distillationthe reaction mixture was distilled
  4. customto remove the dichloromethane
  5. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the obtained residue
  6. extractionThe obtained mixture was extracted with chloroform
  7. concentrationThe obtained chloroform layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c47440760bf0435898d24cf69b5e30c1
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840910

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