Pyridine → 2-Cyano-4,4'-dinitrobenzanilide

HRID 461213

Reaktionsgleichung

Reaktionsgleichung von HRID 461213
[N+:1]([C:4]1[CH:11]=[C:8](C#N)[C:7]([NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].[N:25]1C=CC=C[CH:26]=1>>[C:26]([C:23]1[CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=[CH:18][C:19]=1[C:20]([NH:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:8]=1)=[O:21])#[N:25]

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 285322-Amino-5-nitrobenzonitrile

Produkt 1

HCID 196897482-Cyano-4,4'-dinitrobenzanilide

Versuchsvorschrift

To a stirred solution of 16.3 gm. (0.1 mole) of 5-nitroanthranilonitrile in 100 ml. of dry pyridine is added 18.56 gm. (0.1 mole) of p-nitrobenzoyl chloride. The reaction mixture is refluxed for 3 hours. The pyridine is distilled in vacuo. The oily residue is poured into 600 ml. of water and is distilled in vacuo. The oily residue is poured into 600 ml. of water and the precipitate removed by filtration. The precipitate is boiled with 1500 ml. of ethanol. The insoluble material is removed by filtration. There is obtained 21.57 gm. of yellow solid that melts at 195°-196°.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. distillationThe pyridine is distilled in vacuo
  3. additionThe oily residue is poured into 600 ml
  4. distillationof water and is distilled in vacuo
  5. additionThe oily residue is poured into 600 ml
  6. customof water and the precipitate removed by filtration
  7. customThe insoluble material is removed by filtration
  8. customThere is obtained 21.57 gm

Quellen und Nachweise

ORD-Eintrag
ord-9bb7520d73ab4a81afcf39c912f25f30
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04061791

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