Sodium hydride → HCID 86743626, Verbindung

HRID 477810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477810
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6](=[O:16])[N:7]2[C:12]=1[C:11]1[S:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8]2.[H-].[Na+].Cl[C:26]([N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[O:27]>CN(C)C=O>[O:16]=[C:6]1[N:7]2[NH:8][CH2:9][C:10]3[CH:15]=[CH:14][S:13][C:11]=3[C:12]2=[C:3]([CH2:2][O:1][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH:4]=[C:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 848104-Morpholinecarbonyl chlorideHCID 19913664HCID 19913664, Verbindung

Produkt 1

HCID 86743626HCID 86743626, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2.62 g of 4,5-dihydro-10-(hydroxymethyl)-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazin-7-one are dissolved in 80 ml of N,N-dimethylformamide and cooled to 3° in an ice-bath. 440 mg of 55 percent sodium hydride (NaH) dispersion are added portionwise thereto and the mixture is stirred for an additional hour after the last portion has been added. A solution of 1.5 g of N-chlorocarbonylmorpholine in 3 ml of N,N-dimethylformamide is now added dropwise thereto. The reaction mixture is left to stir at about 5° for an additional 45 minutes and poured into 800 ml of ice-water, whereby the crude product crystallizes out. After washing with water and drying, the crude product is purifed by chromatography on silica gel and recrystallization. There is obtained (4,5-dihydro-7-oxo-8-phenyl-7H-pyrido[1,2-b]-thieno[2,3-d]pyridazin-10-yl)methyl-4-morpholinecarboxylate of m.p. 207°-210° (acetonitrile).

Aufarbeitung

  1. temperaturecooled to 3° in an ice-bath
  2. additionhas been added
  3. waitThe reaction mixture is left
  4. stirringto stir at about 5° for an additional 45 minutes
  5. customcrystallizes out
  6. washAfter washing with water
  7. customdrying
  8. customthe crude product is purifed by chromatography on silica gel and recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-25d629519ec84dab9c66c025c68a8e02
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889854

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