3-Nitroaniline → Benzamide, 3-nitro-N-(3-nitrophenyl)-

HRID 236988

Reaktionsgleichung

Reaktionsgleichung von HRID 236988
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])([O-:20])=[O:19]>C(OCC)(=O)C>[N+:18]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:25])([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-

Produkt 1

HCID 66861Benzamide, 3-nitro-N-(3-nitrophenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

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°.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9dd1c25003a44e3d8fea22c836922611
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04159341

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