Acetonitrile → HCID 178503422, Verbindung

HRID 394479

Reaktionsgleichung

Reaktionsgleichung von HRID 394479
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:13][NH:12][C:11](=[O:25])[CH2:10]2)[CH:6]=[CH:5][N:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(#N)C>CCOCC.CCOC(C)=O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([OH:25])[N:12]=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 181766265-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Produkt 1

HCID 178503422HCID 178503422, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584169Diethylether ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Compound 6 (1.92 g, 5.26 mmol), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (4.78 g, 21.0 mmol), and acetonitrile (30 mL) were combined under argon and heated at 90° C. for 1 h. The solution was cooled and the solvent was removed in vacuo. The crude product was purified by flash column chromatography (methylene chloride:methanol:ammonium hydroxide 95:5:0.5) to give a solid. Trituration with.Et2O EtOAc gave Compound 69: 1.60 g (4.4 mmol, 83%)

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by flash column chromatography (methylene chloride:methanol:ammonium hydroxide 95:5:0.5)
  4. customto give a solid

Quellen und Nachweise

ORD-Eintrag
ord-97f21f61c67445529680a26e4abcd655
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602872B1

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