Sodium hydride → N-(4-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide

HRID 1728855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728855
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=1.[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])=[CH:26][CH:25]=1.[H-].[Na+]>O1CCCC1>[N:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:5][CH:4]=2)[C:32](=[O:34])[CH3:33])=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 289830N-(4-Pyridinylmethyl)acetamideHCID 100228401-(Bromomethyl)-4-(tetradecyloxy)benzene

Produkt 1

HCID 10095404N-(4-Pyridinylmethyl)-N-[[4-(tetradecyloxy)phenyl]methyl]acetamideAusbeute 28,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound is prepared by the procedure of Example 27 using 2.55 g of product from Example 20, 0.999 g of product from Example 15, 0.319 g of washed 50% sodium hydride and 30 ml of tetrahydrofuran. The reaction is stirred at room temperature for hours, heated at reflux temperature for 24 hours; followed by stirring at room temperature for an additional 48 hours. The residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate) to give 0.862 g of the desired product. The spectral data indicates the presence of 2 rotomers.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux temperature for 24 hours
  3. stirringby stirring at room temperature for an additional 48 hours
  4. customThe residue is purified by column chromatography (silica gel: 5% methyl alcohol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c9dc48c36a3047fb8c0dbd7d874caedb
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328921

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