Phosphorus oxychloride → 3-Chlorocinnamonitrile

HRID 596782

Reaktionsgleichung

Reaktionsgleichung von HRID 596782
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]([NH2:9])=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7]#[N:9]

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 656671Sodium PyrosulfiteHCID 534396243-(3-Chlorophenyl)prop-2-enamide

Produkt 1

HCID 3673163-ChlorocinnamonitrileAusbeute 59,5 %

Versuchsvorschrift

m-Chlorocinnamamide (1.39 g.) was mixed with sodium metabisulphite (0.72 g.) and phosphoryl chloride (3 ml.). The mixture was heated on the steam-bath for 2.5 hr. and the phosphoryl chloride removed under reduced pressure. The residue was washed well with water, leaving slightly impure m-chlorocinnamonitrile (0.744 g., 59.5%). Recrystallisation from aqueous acetone gave m-chlorocinnamonitrile, m.p. 56°-57°, λmax. (EtOH) 226, 270 nm. ε 19000, 22500.

Aufarbeitung

  1. temperatureThe mixture was heated on the steam-bath for 2.5 hr
  2. customand the phosphoryl chloride removed under reduced pressure
  3. washThe residue was washed well with water

Quellen und Nachweise

ORD-Eintrag
ord-f89108d6e9ad4052b1035597098795e2
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012377

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