Acetaldehyde → tert-Butyl 2-ethylidenehydrazine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[CH:10](=O)[CH3:11]>C(O)C>[C:6]([O:5][C:1]([NH:2][N:3]=[CH:10][CH3:11])=[O:4])([CH3:9])([CH3:8])[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of tert-butyl carbazate (50.0 g, 0.38 mole) and acetaldehyde (17.5 g, 0.4 mole) in ethanol (250 mL) was refluxed for 72 h. The solution was concentrated in vacuo and dissolved in ethyl acetate. The solution was washed with water, dried (anhydrous sodium sulfate) and concentrated to afford N′-ethylidene-hydrazinecarboxylic acid tert-butyl ester (56 g) as a light yellow oil that solidified on standing. MS (ESI+) for C7H14N2O2 m/z 159.0 (M+H)+.
Workup
- concentrationThe solution was concentrated in vacuo
- dissolutiondissolved in ethyl acetate
- washThe solution was washed with water
- dry with materialdried (anhydrous sodium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a135696105874c1c846421f7898549ec
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960664B2
Reaction notes
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