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

HRID 624625Notes

Reaction equation

HRID 624625 reaction equation
[C:1]([NH:8][NH2:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].S([O-])([O-])(=O)=O.[Mg+2].[CH3:16][C:17]([CH3:19])=O>C(O)(=O)C>[CH3:16][C:17](=[N:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH3:19]

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)carbohydrazide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To a solution of tert-butyl hydrazinecarboxylate 1 (CAS Reg. No. 870-46-2) (25.1 g, 0.190 mol) in acetone (185 mL) was added the magnesium sulfate (6 g) and 12 drops acetic acid (Wu et al (2012) Jour. Med. Chem. 55(6):2724-2736; WO 2007/056170; Zawadzki et al (2003) Polish Jour. Chem. 77(3):315-319). The mixture was heated to reflux for 2.5 h and cooled to rt and filtered. The filtrate was concentrated to give tert-butyl 2-(propan-2-ylidene)hydrazinecarboxylate 2 (CAS Reg. No. 16689-34-2) as 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. 1H NMR 300 MHz (CDCl3) d 7.35 (br s, 1H, NH), 2.04 (s, 3H), 1.82 (s, 3H), 1.54 (s, 9H); 13C NMR 300 MHz (CDCl3) d 152.9, 149.7, 80.7, 28.1, 25.3, 15.9.

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-e6dae2dcc6e1440fbf2237f15771754c
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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