Acetic Acid → N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide

HRID 1874087Notes

Reaction equation

HRID 1874087 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].C(O)(=O)C.[CH3:20][C:21]([CH3:23])=O>>[C:1]([O:5][C:6]([NH:7][N:8]=[C:21]([CH3:23])[CH3:20])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 70091tert-Butyl carbazate

Product 1

HCID 11435207N'-(propan-2-ylidene)(tert-butoxy)carbohydrazide

Procedure

To a solution of tert-butylcarbazate (50.0 g, 378 mmol) in 40 mL acetone is added 10 g MgSO4 and 5 mL acetic acid and the reaction mixture is stirred at reflux temperature for 1 h. The reaction mixture is filtered and concentrated in vacuo. The residue is crystallized from diethyl ether/cyclohexane. Yield: 49.4 g.

Workup

  1. temperatureat reflux temperature for 1 h
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue is crystallized from diethyl ether/cyclohexane

Sources & evidence

ORD record
ord-d1f8b1a159b94a7cb8934a8881dbae1b
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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