Sodium Chloride → N-(2-Pyridinylmethyl)-N-(methylsulfonyl)-4-(tetradecyloxy)benzamide

HRID 248025

Reaktionsgleichung

Reaktionsgleichung von HRID 248025
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].[CH2:15]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[Cl-].[Na+]>O1CCCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:38][CH:37]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 4657001N-(pyridin-2-ylmethyl)methanesulfonamideHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

Produkt 1

HCID 19014924N-(2-Pyridinylmethyl)-N-(methylsulfonyl)-4-(tetradecyloxy)benzamideAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a room temperature solution of 0.428 g of washed 50% sodium hydride in 15 ml of dry tetrahydrofuran is added, via cannula, 1.58 g of product from Example 121 dissolved in 20 ml of dry tetrahydrofuran. The mixture is stirred for 2 hours and 3.0 g of product from Example 3 dissolved in 20 ml of dry tetrahydrofuran is added, via cannula. After stirring at room temperature for 30 minutes, the reaction is heated at reflux temperature for 2 hours. The cooled mixture is poured into half saturated sodium chloride and extracted with chloroform. The organic layer is dried and concentrated in vacuo. The residue is purified by chromatography (silica gel: 15-40% ethyl acetate/hexane) to give 3.85 g of the desired product.

Aufarbeitung

  1. additionis added, via cannula
  2. stirringAfter stirring at room temperature for 30 minutes
  3. temperaturethe reaction is heated
  4. temperatureat reflux temperature for 2 hours
  5. extractionextracted with chloroform
  6. customThe organic layer is dried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by chromatography (silica gel: 15-40% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d1044c7f8f5c471bb0204eee3a29fb07
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208247

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