1,3-Dimethyl-2-imidazolidinone → 1-(2-Phenylphenyliminomethyl)-2-nitroiminoimidazolidine

HRID 1587747

Reaction equation

HRID 1587747 reaction equation
Cl.N1C=CC=CC=1.C(O[CH:11](OCC)[N:12]1[CH2:16][CH2:15][NH:14][C:13]1=[N:17][N+:18]([O-:20])=[O:19])C.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN1CCN(C)C1=O>O>[C:31]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[N:17][N+:18]([O-:20])=[O:19])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 70152-AminobiphenylHCID 10176127Pyridinium chlorideHCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Product 1

HCID 1363314891-(2-Phenylphenyliminomethyl)-2-nitroiminoimidazolidineYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.25 g of pyridine hydrochloride was added to a mixture of 5.0 g of 1-diethoxymethyl-2-nitroiminoimidazolidine, 3.64 g of o-aminobiphenyl and 3 ml of 1,3-dimethyl-2-imidazolidinone at 100° C., followed by agitation at the same temperature for 20 minutes. The reaction mixture was poured into water, extracted with ethyl ether, washed with water, dried and concentrated, followed by addition of ether to the resultant oily residue. The resulting crystals were collected by filtration and dried to give 3.2 g of 1-(2-phenylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. extractionextracted with ethyl ether
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. additionfollowed by addition of ether to the resultant oily residue
  6. filtrationThe resulting crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-1ecdfd67f3694e3b9728a254e610c4d4
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Linked notes

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