Reaktion #519842

Reaktionsgleichung

Water chloroform

3,4-bis-(4-methoxyphenyl)pyridazine 1-oxide

potassium cyanide

benzoyl chloride

→

prisms

Ausbeute 64.0%

3,4-bis-(4-methoxyphenyl)-6-cyanopyridazine

Ausbeute 64.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 20 hours
3. 3
   Extraktionsubsequent to alkalinization, the thus-obtained mixture was extracted with chloroform
4. 4
   WaschenThe organic layer was washed with water
5. 5
   Trocknenwas then dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   Sonstigethe residue (oil) was separated
8. 8
   Sonstigepurified by chromatography on a silica gel column [hexane/ethyl acetate (5/1)]
9. 9
   SonstigeRelevant fractions were crystallized from ethyl acetate-diethyl ether-hexane, whereby the title compound

Vorschrift

A solution of 3,4-bis-(4-methoxyphenyl)pyridazine 1-oxide [Eur. J. Med. Chem.-Chimica Therapeutica, 14, 53-60 (1979)] (5.01 g, 16.25 mmol) and potassium cyanide (3.17 g, 48.75 mmol) in water (90 ml) was ice-cooled. After benzoyl chloride (7.77 g, 55.25 mmol) was added dropwise with vigorous stirring under a nitrogen gas atmosphere, the resulting mixture was stirred at room temperature for 20 hours. Water-chloroform was added to the reaction mixture, and subsequent to alkalinization, the thus-obtained mixture was extracted with chloroform. The organic layer was washed with water, and was then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue (oil) was separated and purified by chromatography on a silica gel column [hexane/ethyl acetate (5/1)]. Relevant fractions were crystallized from ethyl acetate-diethyl ether-hexane, whereby the title compound was obtained as slightly yellow prisms (3.30 g, 64.0%). Melting point: 113-115° C.

Quelle