Formamide → 2-((4-(Diethylamino)phenyl)azo)-5-nitrobenzonitrile

HRID 27678

Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+].[CH:29]([NH2:31])=O.C(OC(=O)C)(=O)C>[Cu]I.C(OCCCC)(=O)C>[C:29]([C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:14]=1)#[N:31]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

2-Bromo-4-nitro-4'-(N,N-diethylamino)azobenzene (1.9 parts), copper (I) iodide (0.95 parts), anhydrous sodium acetate (1.2 parts), formamide (1.8 parts), acetic anhydride (2.0 parts) and n-butyl acetate (44 parts) are mixed together and heated, with stirring, to 110° C. during 15 minutes. The temperatures is maintained at 110° C. for 31/2 hours when reaction is adjudged complete by thin layer chromatography. The solvent is removed at 80° C. under reduced pressure and the residue is slurried in water (250 parts), collected and dried. 2-Cyano-4-nitro-4'-(N,N-diethylamino)azobenzene is obtained in 75% yield and requires no purification.

Aufarbeitung

temperatureheated
temperatureThe temperatures is maintained at 110° C. for 31/
custom2 hours when reaction
customThe solvent is removed at 80° C. under reduced pressure
customcollected
customdried

Quellen und Nachweise

ORD-Eintrag: ord-99c02245faa74ee4a81ad4cfc92bd3be
Quelldatensatz: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04222935

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