Diketene → N-Methyl-N-[3-(3-methyl-1,2,4-triazolo-[4,3-b]-pyridazin-6-yl)phenyl]-3-oxo-butanamide

HRID 35640

Reaktionsgleichung

Reaktionsgleichung von HRID 35640
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:18])=[N:16][N:17]=3)[N:14]=2)[CH:4]=1.[CH2:19]=[C:20]1[O:24][C:22](=[O:23])[CH2:21]1>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([CH3:18])=[N:16][N:17]=3)[N:14]=2)[CH:4]=1)[C:22](=[O:23])[CH2:21][C:20](=[O:24])[CH3:19]

Komponenten

4

Edukt 2

HCID 12661DiketeneHCID 2779723N-Methyl-3-(3-Methyl[1,2,4]Triazolo[4,3-B]Pyridazin-6-Yl)Aniline

Produkt 1

HCID 15595682N-Methyl-N-[3-(3-methyl-1,2,4-triazolo-[4,3-b]-pyridazin-6-yl)phenyl]-3-oxo-butanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2.0 g of N-methyl-3-(3-methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl)benzenamine and 2.14 ml of diketene in 250 ml of dry toluene was heated to reflux for 2 days. The solution was concentrated in vacuo and the residue partitioned between 300 ml dichloromethane and 200 ml of water. The aqueous layer was extracted with 150 ml portions of dichloromethane. The organic layer and extracts were combined, dried and concentrated in vacuo. The residue was chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3). The fractions containing product were combined, evaporated in vacuo and the solid recrystalized from dichloromethane-hexane to give 1.15 g of tan crystals, mp 138°-141° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 days
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue partitioned between 300 ml dichloromethane and 200 ml of water
  5. extractionThe aqueous layer was extracted with 150 ml portions of dichloromethane
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on 300 g of silica gel with dichloromethane-methanol (97:3)
  9. additionThe fractions containing product
  10. customevaporated in vacuo
  11. customthe solid recrystalized from dichloromethane-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d6294640900645d18814bf4b5cb8d64f
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767765

Verknüpfte Notizen

Wird geladen…