P-Toluenesulfonamide → N,N-ditetradecyl-p-toluenesulfonamide

HRID 1596155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596155
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C)C=O.CCOCC>[CH2:19]([N:17]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[S:14]([C:11]1[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=1)(=[O:16])=[O:15])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Komponenten

6

Edukt 3

HCID 6269P-ToluenesulfonamideHCID 8208Myristyl bromideHCID 11430Potassium Carbonate

Produkt 1

HCID 21701141N,N-ditetradecyl-p-toluenesulfonamideAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (20.18 g; 146.00 mmol) is added to a solution of p-toluenesulfonamide (5.00 g; 29.20 mmol) and 1-bromotetradecane (21.70 ml; 73.00 mmol) in dimethylformamide (75 ml). The suspension is stirred for 20 h at reflux; the reaction medium is then cooled to room temperature, diluted with ether (100 ml) and filtered. The filtrate is washed with water (50 ml) and the aqueous phase is extracted with ether (100 ml). The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure to give a white solid which is purified by chromatography on a column of silica gel (eluent: 40/60 dichloromethane/hexane) to give N,N-ditetradecyl-p-toluenesulfonamide (15.86 g; 96%) in the form of a white solid.

Aufarbeitung

  1. temperatureat reflux
  2. filtrationfiltered
  3. washThe filtrate is washed with water (50 ml)
  4. extractionthe aqueous phase is extracted with ether (100 ml)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a white solid which
  9. customis purified by chromatography on a column of silica gel (eluent: 40/60 dichloromethane/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e9ffb329126746eb888dd0d9a9fb51c5
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291423B1

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