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

HRID 432660
Notes
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Reaction equation

HRID 432660 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a8bb3a292521437abdc6780b5f4fa848
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06664256B1

Reaction notes

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