2-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamide → 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1603127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603127
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].O=[C:8]1[C:14]2C=CC=[CH:18][C:13]=2[N:12]([C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:1]=[C:2]1[C:5]2[CH:14]=[CH:8][CH:9]=[CH:10][C:11]=2[N:12]([C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:22][CH:21]=2)[CH2:13][CH2:18][CH2:3]1

Komponenten

5

Edukt 2

HCID 108108812-Methyl-N-[4-[(2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]phenyl]benzamideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 196080415-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepineAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Methyltriphenylphosphonium bromide (4.30 g) is suspended in tetrahydrofuran (100 ml) and thereto is added potassium t-butoxide (1.58 g) under ice-cooling. The mixture is stirred at -5° C. for 1 hour and thereto is added 5-oxo-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.60 g) and the mixture is stirred at room temperature for 1 hour. The reaction solution is poured into ice-water (200 ml) and extracted with ethyl acetate. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2), and recrystallized from ethyl acetate/n-hexane to give 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.34 g) as white powder, m.p. 216-217° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:2)
  8. customrecrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c1c3c967c174f68afb33e0bf9194645
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985869

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