Reaction #334955

ord-8444665459d2468d8aab8aa8be7c80ba

Reaction equation

CCN(CC)CC
triethylamine
O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1
2,4-dinitrofluorobenzene
CCOC(=O)c1c[nH]c(C)n1
ethyl 2-methylimidazole-4-carboxylate
→
CCOC(=O)c1cn(-c2ccc([N+](=O)[O-])cc2[N+](=O)[O-])c(C)n1
Ethyl 1-(2,4-dinitrophenyl)-2-methylimidazole-4-carboxylate

Reactants

CCN(CC)CC
triethylamine
O=[N+]([O-])c1ccc(F)c([N+](=O)[O-])c1
2,4-dinitrofluorobenzene
CCOC(=O)c1c[nH]c(C)n1
ethyl 2-methylimidazole-4-carboxylate

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture was refluxed for 18 hours
  2. 2
    workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
  3. 3
    Otherthe residue was chromatographed

Procedure

16 ml of triethylamine was added to 14.5 g (0.078 mol) of 2,4-dinitrofluorobenzene, 12 g (0.078 mol) of ethyl 2-methylimidazole-4-carboxylate and 500 ml of toluene, and the mixture was refluxed for 18 hours. The solvent was then distilled off under reduced pressure and the residue was chromatographed using pentane/ethyl acetate as mobile phase.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05207820uspto-grants-1993_05