Dimethylformamide → 1-Benzyl-7-chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one

HRID 501432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501432
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.CN(C)C=O.[CH2:14]([N:21]1[C:25]2[C:26]([Cl:31])=[N:27][NH:28][C:29](=O)[C:24]=2[N:23]=[CH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(OCC)(=O)C>[CH2:14]([N:21]1[C:25]2[C:26]([Cl:31])=[N:27][N:28]([CH3:29])[C:1](=[O:4])[C:24]=2[N:23]=[CH:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 574728331-Benzyl-7-chloro-1,5-dihydroimidazo[4,5-d]pyridazin-4-one

Produkt 1

HCID 574728321-Benzyl-7-chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-oneAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.604 g of potassium carbonate and 0.297 ml of methyl iodide were added to a 30 ml N,N-dimethylformamide solution of 1.035 g of 1-benzyl-7-chloro-1,5-dihydroimidazo[4,5-d]pyridazin-4-one (J. A. Carbon Journal of the American Chemical Society, 80, pp. 6083, 1958), and the mixture was stirred at room temperature for 15 hours. 300 ml of ethyl acetate and 100 ml of water were added to the solution, and the organic layer was washed twice with 100 ml of water and then with 100 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.280 g of the title compound was obtained from the fraction eluted with ethyl acetate.

Aufarbeitung

  1. washthe organic layer was washed twice with 100 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9c0c6ae43fd34ef1b22b194146871b42
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772226B2

Notizen zur Reaktion

Wird geladen…