Nitrobenzene → 2-oxo-3-tert-butoxycarbonylamino-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1979346
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH:16]=[CH:15]2)[CH2:4][CH:3]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[N+](C1C=CC=CC=1)([O-])=O>C1(C)C(C)=CC=CC=1.[C].[Pd]>[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:4][CH:3]1[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Komponenten

5

Edukt 2

HCID 7416NitrobenzeneHCID 212015412-oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexene-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 212017702-oxo-3-tert-butoxycarbonylamino-5-phenyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

2-Oxo-3-tert-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (500 mg) was suspended in xylene (20 ml), nitrobenzene (831 mg) and 10% palladium carbon (250 mg) were added therto, and the mixture was refluxed for 2 hours. The reaction mixture was allowed to cool, filtrated, and the filtrate was concentrated under reduced pressure. Diisopropyl ether was added to the residue, crystals so precipitated were collected by filtration, to thereby obtain 413 mg of the titled compound (Yield: 83%).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. temperatureto cool
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionDiisopropyl ether was added to the residue, crystals
  6. customso precipitated
  7. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9ab8b04b09084eb4acce0b6b02ef6938
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239131B1

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