Water → 1-(4-Isopropylphenyliminomethyl)-2-nitroiminoimidazolidine

HRID 1587738Notes

Reaction equation

HRID 1587738 reaction equation
S(=O)(=O)(O)O.[CH:6]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([CH3:8])[CH3:7].CN1CCN(C)C1=O.O.C(O[CH:28](OCC)[N:29]1[CH2:33][CH2:32][NH:31][C:30]1=[N:34][N+:35]([O-:37])=[O:36])C>>[CH:6]([C:9]1[CH:15]=[CH:14][C:12]([N:13]=[CH:28][N:29]2[CH2:33][CH2:32][NH:31][C:30]2=[N:34][N+:35]([O-:37])=[O:36])=[CH:11][CH:10]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 74644-IsopropylanilineHCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Product 1

HCID 1363314851-(4-Isopropylphenyliminomethyl)-2-nitroiminoimidazolidineYield 41.6%

Procedure

0.05 g of concentrated sulfuric acid was dropped in a mixture of 5.0 g of 1-diethoxymethyl-2-nitroiminoimidazolidine, 2.48 g of p-isopropylaniline and 2 ml of 1,3-dimethyl-2-imidazolidinone at 110° C., followed by agitation at the same temperature for 1 hour. 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 obtain 2.1 g of 1-(4-isopropylphenyliminomethyl)-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-90ef4de4147945ed80cb39b27f60a45d
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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