1,3-Dimethyl-2-imidazolidinone → 1-Diethoxymethyl-2-nitroiminoimidazolidine

HRID 258120

Reaction equation

HRID 258120 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].[CH:10]([O-:15])([O-])[O:11][CH2:12][CH3:13].CN1[CH2:21][CH2:20]N(C)C1=O>O>[CH2:20]([O:15][CH:10]([O:11][CH2:12][CH3:13])[N:6]1[CH2:7][CH2:8][NH:9][C:5]1=[N:4][N+:1]([O-:3])=[O:2])[CH3:21]

Participants

5

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 53630039EthylorthoformateHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g of 2-nitroiminoimidazolidine, 100 g of ethyl orthoformate and 25 ml of 1,3-dimethyl-2-imidazolidinone was heated under reflux for 3 hours. After cooling to room temperature, the mixture was poured into water, followed by extraction with ethyl acetate. After washing with water, the extract was dried with anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The resultant crystals were sludged with ether to give 32 g of 1-diethoxymethyl-2-nitroiminoimidazolidine.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe extract was dried with anhydrous magnesium sulfate
  6. distillationafter which the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6d6a20cb54b64732b2db00d40b533e37
Source dataset
uspto-grants-1993_11
Patent number
US05264584

Linked notes

Loading…