Myristyl bromide → N,N-Diethyl-2-(tetradecyloxy)benzamide

HRID 247928

Reaktionsgleichung

Reaktionsgleichung von HRID 247928
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=1)[OH:7])[CH3:2].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4](=[O:12])[C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[O:7][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH3:14]

Komponenten

5

Edukt 3

HCID 8208Myristyl bromideHCID 11430Potassium CarbonateHCID 88006Diethylsalicylamide

Produkt 1

HCID 19016298N,N-Diethyl-2-(tetradecyloxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 25 g of N,N-diethylsalicylamide, 38.5 ml of 1-bromotetradecane, 22.35 g of potassium carbonate and 400 ml of 2-butanone is heated at reflux temperature for 16 hours. The reaction is cooled, filtered and concentrated in vacuo. The concentrate is dissolved in chloroform, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-30% ethyl acetate/hexane) to give 42.5 g of the desired product as colorless crystals.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction is cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe concentrate is dissolved in chloroform
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by column chromatography (silica gel:0-30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-abd0eef33caf43baafbb8f4403bcda70
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208247

Verknüpfte Notizen

Wird geladen…