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

HRID 2400524Notes

Reaction equation

HRID 2400524 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].S([O-])([O-])(=O)=O.[Mg+2].[CH3:16][C:17]([CH3:19])=O>C(O)(=O)C>[C:17](=[N:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])([CH3:19])[CH3:16]

Participants

5

Reactant 3

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

Product 1

HCID 11435207N'-(propan-2-ylidene)(tert-butoxy)carbohydrazideYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a mechanically stirred solution of tert-butylcarbazate (450 g, 3.4 mol) in acetone (2.5 L) was added magnesium sulfate (100 g, 0.83 mol) and 100 drops of acetic acid. The mixture was warmed to reflux and stirred for 3.5 h. After being cooled to rt, the mixture was filtered and partially concentrated, at which point the product crystallized from the supersaturated solvent. The crystals were filtered and dried in a vacuum oven overnight to provide the title compound as colorless needles (463 g, 79%): 1H NMR (300 MHz, d6-DMSO) δ 1.40 (s, 9H), 1.75 (s, 3H), 1.83 (s, 3H).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. filtrationthe mixture was filtered
  4. concentrationpartially concentrated, at which point the product
  5. customcrystallized from the supersaturated solvent
  6. filtrationThe crystals were filtered
  7. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-c45abd0a0a46464685f8310a389de814
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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