Potassium Carbonate → 1-(3,3-Dimethyl-2-butanon-1-yl)-2-nitroimino-imidazolidine

HRID 1638836

Reaction equation

HRID 1638836 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(#N)C>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18](=[O:23])[CH2:17][N:6]1[CH2:7][CH2:8][NH:9][C:5]1=[N:4][N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1363645641-(3,3-Dimethyl-2-butanon-1-yl)-2-nitroimino-imidazolidineYield 76.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.6 g of 2-nitroimino-imidazolidine, 3.0 g of anhydrous potassium carbonate and 30 ml of dry acetonitrile was stirred at room temperature for 30 minutes. Then, 2.7 g of 1-chloro-3,3-dimethyl-2-butanone were added to the mixture under stirring at room temperature. The reaction mixture was heated and refluxed for 1 hour. The acetonitrile was distilled off under a reduced pressure, and the residue was admixed with water. The aimed product was separated by filtration. The crystalline product was washed in ether and dried. 3.5 g of 1-(3,3-dimethyl-2-butanon-1-yl)-2-nitroimino-imidazolidine were obtained. mp. 158°-159° C.

Workup

  1. stirringunder stirring at room temperature
  2. temperatureThe reaction mixture was heated
  3. temperaturerefluxed for 1 hour
  4. distillationThe acetonitrile was distilled off under a reduced pressure
  5. customThe aimed product was separated by filtration
  6. washThe crystalline product was washed in ether
  7. customdried

Sources & evidence

ORD record
ord-416ed71b3d104763a56fa07d5e6228e9
Source dataset
uspto-grants-1989_11
Patent number
US04880933

Linked notes

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