1,3-Dimethyl-2-imidazolidinone → HCID 137226492, compound

HRID 1587742Notes

Reaction equation

HRID 1587742 reaction equation
C(O[CH:4](OCC)[N:5]1[CH2:9][CH2:8][NH:7][C:6]1=[N:10][N+:11]([O-:13])=[O:12])C.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([F:27])([F:26])[F:25].CN1CCN(C)C1=O>O>[F:25][C:24]([F:26])([F:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:17]=[CH:4][N:5]1[CH2:9][CH2:8][NH:7][C:6]1=[N:10][N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 69222-(Trifluoromethyl)anilineHCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Product 1

HCID 137226492HCID 137226492, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.05 g of boron trifluoride ether complex was added under ice-cooling conditions to a mixture of 5.0 g of 1-diethoxymethyl-2-nitroiminoimidazolidine, 3.47 g of o-aminobenzotrifluoride and 5 ml of 1,3-dimethyl-2-imidazolidinone. Immediately, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried and concentrated. Ether was added to the resultant oily residue and the resultant crystals were removed by filtration, followed by washing with hot ethyl acetate to give 3.43 g of 1-(2-trifluoromethylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. addition0.05 g of boron trifluoride ether complex was added under ice-
  2. temperaturecooling conditions
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. additionEther was added to the resultant oily residue
  8. customthe resultant crystals were removed by filtration
  9. washby washing with hot ethyl acetate

Sources & evidence

ORD record
ord-7038d678ad944d9c8c088500cd1bf345
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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