Acetaldehyde → tert-Butyl 2-ethylidenehydrazine-1-carboxylate

HRID 1062325Notes

Reaction equation

HRID 1062325 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

HCID 177AcetaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 57358255tert-Butyl 2-ethylidenehydrazine-1-carboxylateYield 93.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washThe solution was washed with water
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a135696105874c1c846421f7898549ec
Source dataset
uspto-grants-2005_11
Patent number
US06960664B2

Reaction notes

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