Acetonitrile → 3-Amino-3-(4-chlorophenyl)prop-2-enenitrile

HRID 46557

Reaktionsgleichung

Reaktionsgleichung von HRID 46557
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H-].[Na+].[C:12](#[N:14])[CH3:13]>CCOCC.O.CO.C(O)(C)C>[NH2:7][C:6]([C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH:13][C:12]#[N:14]

Komponenten

8

Edukt 3

HCID 6342AcetonitrileHCID 121634-ChlorobenzonitrileHCID 24758Sodium hydride

Produkt 1

HCID 14848883-Amino-3-(4-chlorophenyl)prop-2-enenitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a mixture of 68.5 g. of p-chlorobenzonitrile and 24.0 g. of sodium hydride (50% in mineral oil) in 250 ml. of ether is added, 26.1 ml. of acetonitrile and 2 ml. of isopropanol. The mixture is stirred and refluxed on a steam bath for 6 hours and then stirred overnight at room temperature. A 5 ml. portion of methanol and 250 ml. of water are added. The ether is boiled away on a steam bath and the mixture is filtered. The solid is dissolved in warm ethyl acetate and filtered. The filtrate is evaporated to a solid giving β-amino-4-chlorocinnamonitrile.

Aufarbeitung

  1. additionTo a mixture of 68.5 g
  2. temperaturerefluxed on a steam bath for 6 hours
  3. stirringstirred overnight at room temperature
  4. filtrationthe mixture is filtered
  5. dissolutionThe solid is dissolved in warm ethyl acetate
  6. filtrationfiltered
  7. customThe filtrate is evaporated to a solid

Quellen und Nachweise

ORD-Eintrag
ord-b7a1a5518949456f9e3d128f0626a445
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173650

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