(Phenylmethyl)hydrazine → (+/-)-3-Benzyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione

HRID 36868

Reaktionsgleichung

Reaktionsgleichung von HRID 36868
[CH:1]12[C:7](=[O:8])O[C:4](=[O:5])[CH:2]1[CH2:3]2.[CH2:9]([NH:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[CH2:9]([N:16]1[NH:17][C:7](=[O:8])[CH:1]2[CH:2]([CH2:3]2)[C:4]1=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 11157(Phenylmethyl)hydrazineHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Produkt 1

HCID 10680232(+/-)-3-Benzyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dioneAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

In 150 ml of acetonitrile was dissolved 42 g (374 mmol) of 1,2-cyclopropanedicarboxylic acid anhydride, and to the solution was added dropwise a solution of 45.8 g (374 mmol) of benzylhydrazine in 50 ml of acetonitrile, and the mixture was heated under reflux for 15 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography. Crystallization from ethyl acetate gave 24.1 g (29.7%) of the titled compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by silica gel column chromatography
  5. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fa4eb2357689441a9fe836f52ad71c32
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418232

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