Bromoacetone → 6-Chloro-2,8-dimethyl-imidazo[1,2-b]pyridazine

HRID 1160777

Reaktionsgleichung

Reaktionsgleichung von HRID 1160777
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].Br[CH2:11][C:12](=O)[CH3:13]>C(#N)C>[Cl:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]2[N:3]([CH:11]=[C:12]([CH3:13])[N:1]=2)[N:4]=1

Komponenten

4

Edukt 2

HCID 11715BromoacetoneHCID 123536646-Chloro-4-methylpyridazin-3-amine

Produkt 1

HCID 122483406-Chloro-2,8-dimethyl-imidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Amino-6-chloro-4-methylpyridazine (5.50 g, 38.3 mmol) and bromoacetone (6.90 g, 40.0 mmol) were heated in acetonitrile (50.0 ml) for 8 hours under reflux. The reaction solution was concentrated under reduced pressure, and water (100 ml) was added to the residues which were then adjusted to pH 9 with 20% aqueous sodium hydroxide and extracted twice with ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate and concentrated, and the residues were purified by silica gel column chromatography (ethyl acetate:chloroform=1:2), to give the title compound as white crystals. The yield was 3.80 g (54.6%).

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationThe reaction solution was concentrated under reduced pressure, and water (100 ml)
  3. additionwas added to the residues which
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe residues were purified by silica gel column chromatography (ethyl acetate:chloroform=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-990a68adc2e24486b262b7c0eb65937f
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816526B2

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