2-bromo-N-(2,6-dimethylphenyl)butanamide → N-(2-phthalimido-butyryl)-2,6-dimethyl-aniline

HRID 1649988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649988
Br[CH:2]([CH2:14][CH3:15])[C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])=[O:4].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C)C=O>[C:16]1(=[O:26])[N:20]([CH:2]([CH2:14][CH3:15])[C:3]([NH:5][C:6]2[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:13])=[O:4])[C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12

Komponenten

4

Edukt 2

HCID 130108042-bromo-N-(2,6-dimethylphenyl)butanamideHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 19855569N-(2-phthalimido-butyryl)-2,6-dimethyl-anilineAusbeute 71,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 20.0 g (74 mmoles) of N-(2-bromo-butyryl)--2,6-dimethyl-aniline, 27.8 g (0.15 moles) of potassium phthalimide and 150 ml of dry dimethyl formamide is stirred at 60° C. for 2 hours. The mixture is cooled, poured onto 750 ml of ice water, the separated crystalline substance is filtered off, washed with water and dried. The resulting crude product, weighing 35.7 g, is dissolved in 200 ml of chloroform, the solution is washed thrice with 50 ml of 1 n aqueous sodium hydroxide solution and thrice with 50 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 17.7 g (71.1%) of N-(2-phthalimido-butyryl)-2,6-dimethyl-aniline are obtained; m.p.: 195°-196° C.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. filtrationthe separated crystalline substance is filtered off
  3. washwashed with water
  4. customdried
  5. dissolutionis dissolved in 200 ml of chloroform
  6. washthe solution is washed thrice with 50 ml of 1 n aqueous sodium hydroxide solution and thrice with 50 ml of water
  7. dry with materialeach, dried over anhydrous magnesium sulfate
  8. customthe solvent is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8a7fddd1c6384d6eae1912f0f7b9ff2e
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04922021

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