2-Aminobenzonitrile → 2-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrile

HRID 274132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274132
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=O>C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([N+:19]([O-:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=[N:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

4

Edukt 2

HCID 729132-AminobenzonitrileHCID 118051105-Methyl-2-nitrobenzaldehyde

Produkt 1

HCID 200945252-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrileAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Toluene (167 ml) and 2-aminobenzonitrile (19.7 g, 167 mmol) were added to 5-methyl-2-nitrobenzaldehyde (27.5 g, 167 mmol) as obtained in Reference Example 1, and the mixture was stirred and refluxed for 14 hours, followed by cooling. The resultant crystals were filtered off, washed with a mixed solvent of hexane/toluene (2:1, 150 ml) and hexane (150 ml) twice to give 27.5 g of 2-[N-(5-methyl-2-nitrobenzylidene)amino]benzonitrile. In addition, the solid precipitated from the filtrate was filtered off and washed with hexane (100 ml and 50 ml) to give 10.0 g of the compound.

Aufarbeitung

  1. customas obtained in Reference Example 1
  2. temperaturerefluxed for 14 hours
  3. temperatureby cooling
  4. filtrationThe resultant crystals were filtered off
  5. washwashed with a mixed solvent of hexane/toluene (2:1, 150 ml) and hexane (150 ml) twice

Quellen und Nachweise

ORD-Eintrag
ord-9274c858a04045b6946923ef4ef2faa2
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387684

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