Ethyl cyanoacetate → 6-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile

HRID 1584718

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9](=[N:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.C(O[C:26](=[O:30])[CH2:27][C:28]#[N:29])C.C([O-])(=O)C.[NH4+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:10]([CH3:11])=[C:27]([C:28]#[N:29])[C:26](=[O:30])[N:14]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[N:13]=2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A flask equipped with a claisen distillation head and magnetic stirring was charged with an intimate mixture of 32.6 g (0.097 mole) 1[(4-chlorophenyl)thio]-1-[(4-methoxyphenyl) hydrazono]-2-propanone, 24.8 ml of ethylcyanoacetate and 12.2 g of ammonium acetate. The mixture was heated under a nitrogen atmosphere at 160° C. for 30 min. The reaction mixture was cooled and dissolved in methylene chloride. The organic layer was washed successively with saturated aqueous sodium bicarbonate and water. The organic layer was dried over magnesium sulfate and evaporated in vacuo to yield semi pure product. The residue was recrystallized from 1900 ml of ethanol to yield 6-[(4-chlorophenyl)thio]-2,3-dihydro-2-(4-methoxyphenyl)-5-methyl-3-oxo-4-pyridazinecarbonitrile, mp 146-148° C. (EtOH).

Aufarbeitung

customA flask equipped with a claisen distillation head
temperatureThe reaction mixture was cooled
washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and water
dry with materialThe organic layer was dried over magnesium sulfate
customevaporated in vacuo
customto yield semi pure product
customThe residue was recrystallized from 1900 ml of ethanol

Quellen und Nachweise

ORD-Eintrag: ord-11af52a3fa3b4bfba8a5400c45b6a72f
Quelldatensatz: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05935945

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