2-Bromopropane → N-isobutyl-4-isopropyloxyphthalimide

HRID 1792937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792937
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6](=[O:7])[C:5]2=[CH:15][CH:16]=1.Br[CH:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:11]([N:8]1[C:9](=[O:10])[C:4]2=[CH:3][C:2]([O:1][CH:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=[C:5]2[C:6]1=[O:7])[CH:12]([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 220254644-hydroxy-N-isobutylphthalimide

Produkt 1

HCID 22025411N-isobutyl-4-isopropyloxyphthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1 g of 4-hydroxy-N-isobutylphthalimide, 0.85 cm3 of 2-bromopropane and 1.38 g of potassium carbonate in 5 cm3 of dimethylformamide is stirred at a temperature in the region of 60° C. for 17 hours. The reaction mixture is then cooled to a temperature in the region of 20° C. and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° c. The residue is taken up in 70 cm3 of water and then extracted 3 times with 75 cm3 of ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.16 g of N-isobutyl-4-isopropyloxyphthalimide are thus obtained in the form of a white solid. (Rf=0.50, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to a temperature in the region of 20° C.
  2. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° c
  3. extractionextracted 3 times with 75 cm3 of ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-c5f237b2d7c84b948202dfeb7e36f388
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078428B2

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