Benzaldehyde → N-benzylidene-3,5-dichloroaniline

HRID 47093

Reaktionsgleichung

Reaktionsgleichung von HRID 47093
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C>C1(C)C=CC=CC=1>[CH:10](=[N:5][C:4]1[CH:3]=[C:2]([Cl:1])[CH:8]=[C:7]([Cl:9])[CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 297MethaneHCID 122813,5-DichloroanilineHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 962139N-benzylidene-3,5-dichloroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a reaction flask, equipped with a Dean-Stark trap, is added 3,5-dichloroaniline (16.2 g., 0.10 mole), benzaldehyde (10.6 g., 0.10 mole), p-toluenesulfonic acid monohydrate (0.2 g.), and toluene (100 ml.). The reaction mixture is then warmed to reflux and the water (1.65 ml.) collected by azeotroping. The cooled reaction mixture is treated with charcoal and the filtrate reduced in vacuo to give an amber oil that crystallizes on standing to give N-benzylidene-3,5-dichloroaniline which is recrystallized from pentane. m.p. 52°-53° C.

Aufarbeitung

  1. customTo a reaction flask, equipped with a Dean-Stark trap
  2. temperatureThe reaction mixture is then warmed
  3. temperatureto reflux
  4. customthe water (1.65 ml.) collected
  5. customby azeotroping
  6. customThe cooled reaction mixture
  7. customto give an amber oil that
  8. customcrystallizes

Quellen und Nachweise

ORD-Eintrag
ord-1d533b0ee12a4551bfa21b47f1cc1c56
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176198

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