Réaction #65146

Équation de réaction

1,2-cyclopropanedicarboxylic acid anhydride

benzylhydrazine

→

titled compound

Rendement 29.8%

(±)-3-Benzyl-3,4-diazabicyclo[4.1.0]heptane-2,5-dione

Rendement 29.8%

Solvants

acetonitrile

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureunder reflux for 15 hours
3. 3
   AutreThe solvent was removed by distillation under reduced pressure
4. 4
   Autrethe residue was purified by silica gel column chromatography
5. 5
   AutreCrystallization from ethyl acetate

Mode opératoire

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.

Source