Water → 6-(4-Nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

HRID 342315

Reaktionsgleichung

Reaktionsgleichung von HRID 342315
[H-].[Na+].[N+:3]([C:6]1[CH:28]=[CH:27][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[NH:23][C:24]([CH3:26])=[N:25][C:15]=3[CH2:14][CH2:13]2)=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH3:29]I.O>CN(C)C=O.C(Cl)(Cl)Cl>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]([N:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[N:23]=[C:24]([CH3:26])[N:25]([CH3:29])[C:15]=3[CH2:14][CH2:13]2)=[O:11])=[CH:27][CH:28]=1)([O-:5])=[O:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418238HCID 178418238, Verbindung

Produkt 1

HCID 699555616-(4-Nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

In a stream of argon, 144 mg of 60% sodium hydride was suspended in a small volume of N,N-dimethylformamide to which, with cooling on an ice bath, was then added dropwise a solution prepared by dissolving 500 mg of 6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine in 20 ml of N,N-dimethylformamide. After 1 hour of stirring at room temperature, the reaction solution was mixed with 0.11 ml of methyl iodide and stirred for 24 hours at room temperature. The reaction solution was mixed with water and chloroform, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography to obtain 351 mg of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine from the chloroform-methyl alcohol (30:1) eluate.

Aufarbeitung

  1. temperaturewith cooling on an ice bath
  2. additionwas then added dropwise a solution
  3. customprepared
  4. stirringstirred for 24 hours at room temperature
  5. customthe resulting organic layer was separated
  6. washwashed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing the solvent
  9. distillationby distillation under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d0b5a07ed41b46cc88d75079cf656a9f
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856564

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