Water → 1-(2-n-Propylphenyliminomethyl)-nitroiminoimidazolidine

HRID 1587737Notes

Reaction equation

HRID 1587737 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[NH2:13])[CH2:9][CH3:10].CN1CCN(C)C1=O.O.C(O[CH:30](OCC)[N:31]1[CH2:35][CH2:34][NH:33][C:32]1=[N:36][N+:37]([O-:39])=[O:38])C>>[CH2:8]([C:11]1[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=1[N:13]=[CH:30][N:31]1[CH2:35][CH2:34][NH:33][C:32]1=[N:36][N+:37]([O-:39])=[O:38])[CH2:9][CH3:10]

Participants

6

Reactant 5

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 157592-PropylanilineHCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Product 1

HCID 1363314791-(2-n-Propylphenyliminomethyl)-nitroiminoimidazolidineYield 31.7%

Procedure

0.05 g of trifluoroacetic acid was dropped in a mixture of 5.0 g of 1-diethoxymethyl-2-nitroiminoimidazolidine, 2.48 g of o-n-propylaniline and 2 ml of 1,3-dimethyl-2-imidazolidinone at 90° C., followed by agitation at the same temperature for 45 minutes. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried and evaporated. Ether was added to the resultant oily residue and the resultant crystals were separated by filtration and dried to give 1.6 g of 1-(2-n-propylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. additionEther was added to the resultant oily residue
  6. customthe resultant crystals were separated by filtration
  7. customdried

Sources & evidence

ORD record
ord-c27990dcc2e14504beb5d4846ea6d595
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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