Cyclobutanone → tert-Butyl cyclobutylidenecarbazate
Reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([NH:13][NH2:14])=[O:12])([CH3:9])([CH3:8])[CH3:7]>CCCCCC>[C:6]([O:10][C:11]([NH:13][N:14]=[C:1]1[CH2:4][CH2:3][CH2:2]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The reaction mixture of cyclobutanone (15 g, 214 mmol) and hydrazinecarboxylic acid tert-butyl ester (28.3 g, 214 mmol) in hexane (225 mL) was heated to reflux for 2 hours. After cooling down, a precipitate formed and the solid was filtered under vacuum. Isopropanol (10 mL) and hexane (100 mL) were added to the solid and the mixture was put on the rotary evaporator under vacuum until a slurry was generated. After filtration, the solid was washed with hexane twice and dried in vacuo to afford N′-cyclobutylidene-hydrazinecarboxylic acid tert-butyl ester (32 g, 81%) as white solid which was used without further purification.