Thionyl Chloride → 2-Chloromethyl-4-(4-methoxybutoxy)pyridine

HRID 727915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727915
O[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:18])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:18][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 151662242-Hydroxymethyl-4-(4-methoxybutoxy)pyridine

Produkt 1

HCID 151662232-Chloromethyl-4-(4-methoxybutoxy)pyridineAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.6 g of crude 2-hydroxymethyl-4-(4-methoxybutoxy)pyridine was dissolved in 80 ml of chloroform to obtain a solution. A solution of 3.8 g of thionyl chloride in 10 ml of chloroform was dropwise added to this solution at 0° C. The obtained mixture was stirred at 0° C. for one hour. After the completion of the reaction, the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with 200 ml of chloroform twice. The extract was dried over magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The obtained residue was dried in a vacuum to obtain 5.09 g of the title compound as a crude oil.

Aufarbeitung

  1. customto obtain a solution
  2. customAfter the completion of the reaction
  3. extractionextracted with 200 ml of chloroform twice
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled
  7. customto remove the solvent
  8. customThe obtained residue was dried in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ff8c075ea08747978c5d01a318dd9bd7
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05045552

Notizen zur Reaktion

Wird geladen…