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

HRID 1973006Notes

Reaction equation

HRID 1973006 reaction equation
[NH:1]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:2].S([O-])([O-])(=O)=O.[Mg+2].[CH3:16][C:17]([CH3:19])=O>C(O)(=O)C>[C:17](=[N:2][NH:1][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])([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 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a solution of tert-butyl hydrazinecarboxylate (25.1 g, 0.190 mol) in acetone (185 mL) was added the magnesium sulfate (6 g) and 12 drops acetic acid. The mixture was heated to reflux for 2.5 h and cooled to rt and filtered. The filtrate was concentrated to give an off-white solid (32 g, 98%) (used in the next step without further purification). LC-MS [M+H]+=172.9, RT=2.11 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-80945dec405248e7831b8c42383046e7
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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