Reaktion #93887

ord-007f725a2f0c42c8b0ae46b5a365c8aa

Reaktionsgleichung

Nc1cccc([N+](=O)[O-])c1
m-nitroaniline
CCN(CC)CC
triethylamine
O=C(Cl)c1cccc([N+](=O)[O-])c1
m-nitrobenzoylchloride
→
O=C(Nc1cccc([N+](=O)[O-])c1)c1cccc([N+](=O)[O-])c1
3,3'-Dinitrobenzanilide

Edukte

Nc1cccc([N+](=O)[O-])c1
m-nitroaniline
CCN(CC)CC
triethylamine
O=C(Cl)c1cccc([N+](=O)[O-])c1
m-nitrobenzoylchloride

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONTo the solution is added a solution of 18.56 g
  2. 2
    TemperaturThe mixture is refluxed for 6.5 hours
  3. 3
    SonstigeThe precipitate is removed by filtration
  4. 4
    SonstigeThe filtrate is evaporated to dryness in vacuo
  5. 5
    SonstigeThe residue is recrystallized from absolute ethanol
  6. 6
    SonstigeThere is obtained 5.79 g
  7. 7
    Sonstigethat melt at 188°-189°

Vorschrift

To a stirred solution of 13.81 g. (0.1 mole) of m-nitroaniline in 100 ml. of dry ethyl acetate is added 11.13 g. (0.11 mole) of triethylamine. To the solution is added a solution of 18.56 g. (0.1 mole) of m-nitrobenzoylchloride in 100 ml of ethyl acetate. The mixture is refluxed for 6.5 hours. The reaction mixture is allowed to stand at room temperature overnight. The precipitate is removed by filtration. The filtrate is evaporated to dryness in vacuo. The residue is recrystallized from absolute ethanol. There is obtained 5.79 g. of yellow needles that melt at 188°-189°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04128570uspto-grants-1978_12