Methylhydrazine → 3,4-Diazabicyclo[4.1.0]heptane-2,5-dione, 3,7,7-trimethyl-
Reaction equation
[CH3:1][C:2]1([CH3:10])[CH:4]2[C:5]([O:7][C:8](=O)[CH:3]12)=[O:6].[CH3:11][NH:12][NH2:13]>C(O)C>[CH3:11][N:12]1[NH:13][C:5](=[O:6])[CH:4]2[CH:3]([C:2]2([CH3:10])[CH3:1])[C:8]1=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 5 ml of ethyl alcohol were added 949 mg (6.77 mmol) of 3,3-dimethyl-1,2-cyclopropanedicarboxylic acid anhydride and 0.36 ml (6.77 mmol) of methylhydrazine, and the mixture was heated under reflux for 16 hours. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography. Recrystallization from ethyl acetate/hexane afforded 312 mg (27.3%) of the titled compound.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 16 hours
- customThe solvent was removed by distillation under reduced pressure
- customthe residue was purified by silica gel column chromatography
- customRecrystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-2a6cd7bfa9714d75963585c41e32f66f
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05418232
Reaction notes
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