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Benzoyl chloride → 5,6-Bis(4-methoxyphenyl)pyridazine-3-carbonitrile

HRID 432660
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 432660
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N+:11]([O-])[CH:12]=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[C-:24]#[N:25].[K+].C(Cl)(=O)C1C=CC=CC=1.O.C(Cl)(Cl)Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][C:12]([C:24]#[N:25])=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 12568122HCID 12568122, VerbindungHCID 22418719Chloroform water

Produkt 1

HCID 99015025,6-Bis(4-methoxyphenyl)pyridazine-3-carbonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturecooled
  2. stirringthe resulting mixture was stirred at room temperature for 20 hours
  3. extractionsubsequent to alkalinization, the thus-obtained mixture was extracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue (oil) was separated
  8. custompurified by chromatography on a silica gel column [hexane/ethyl acetate (5/1)]
  9. customRelevant fractions were crystallized from ethyl acetate-diethyl ether-hexane, whereby the title compound

Quellen und Nachweise

ORD-Eintrag
ord-a8bb3a292521437abdc6780b5f4fa848
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06664256B1

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