Water → 4,4-Dimethyl-1-n-butyl-2-undecyl-2-imidazoline

HRID 2352208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352208
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1([CH3:23])[CH2:11][NH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N:8]1.BrCCCC.O>CCCCCC.C1C=CC=CC=1>[CH3:6][C:7]1([CH3:23])[CH2:11][N:10]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[N:8]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8002Butyl bromideHCID 178418339ButyllithiumHCID 1784428094,4-Dimethyl-2-undecyl-2-imidazoline

Produkt 1

HCID 146517984,4-Dimethyl-1-n-butyl-2-undecyl-2-imidazolineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

22 ml (55 mmoles) of a 2.5M solution of butyl lithium in hexane are added to 12.62g (50 mmoles) of 4,4-dimethyl-2-undecyl-2-imidazoline in 50 ml of anhydrous benzene at a temperature kept at around 20° C. The mixture is then stirred for 2 hours at ambient temperature (15° to 20° C.). 8.22 g (60 mmoles) of 1 -bromobutane is then added dropwise to the reaction mixture, keeping the temperature at around 20° C. The reaction mixture is then stirred at ambient temperature until it is homogeneous, after which it is refluxed for 3 hours. After cooling, 50 ml of water is added, the mixture is stirred for half hour, decanted and extracted with 100 ml of ether. After drying over magnesium sulfate the solvent is removed in vacuo and the oil is distilled at reduced pressure to give 10.34 g (67%) of the product.

Aufarbeitung

  1. customkept at around 20° C
  2. customat around 20° C
  3. stirringThe reaction mixture is then stirred at ambient temperature until it
  4. temperatureafter which it is refluxed for 3 hours
  5. temperatureAfter cooling
  6. stirringthe mixture is stirred for half hour
  7. customdecanted
  8. extractionextracted with 100 ml of ether
  9. dry with materialAfter drying over magnesium sulfate the solvent
  10. customis removed in vacuo
  11. distillationthe oil is distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac3ad2ecf40a4184a46131587ded5c24
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04876249

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