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Imidazole → HCID 22409067, Verbindung

HRID 1712438
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1712438
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][O:12][CH3:13]>CN(C)C=O>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropane

Produkt 1

HCID 22409067HCID 22409067, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The mixture of 5.02 g of imidazole and 50 ml of N,N-dimethylformamide is admixed at 0° C. with 3.52 g of sodium hydride dispersion (69%) and stirred at room temperature over 1 hour. The solution of 8.36 g of 1-chloro-3-methoxypropane in 10 ml of N,N-dimethylformamide is added and the reaction solution is subsequently stirred at 60° C. over 2 hours. The reaction mixture is cooled, poured onto ice-water (150 ml) and extracted with ethyl acetate (3×150 ml). The organic phases are washed with water (3×150 ml) and brine (150 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (200:20:1 dichloromethane-methanol-conc. ammonia); Rt=1.55.

Aufarbeitung

  1. stirringthe reaction solution is subsequently stirred at 60° C. over 2 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto ice-water (150 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. washThe organic phases are washed with water (3×150 ml) and brine (150 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-70039098ea6040d0b3ffe69d263c49ce
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07790715B2

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