3-Chloropropane-1-sulfonamide → 3-Chloro-6[(3-sulfamoylpropyl)thio]imidazo[1,2-b]pyridazine

HRID 1590068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590068
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[SH2:9].[K].C(O)C.C[O-].[Na+].CO.[Cl:19][C:20]1[N:24]2[N:25]=[C:26](Cl)[CH:27]=[CH:28][C:23]2=[N:22][CH:21]=1>CO>[Cl:19][C:20]1[N:24]2[N:25]=[C:26]([S:9][CH2:2][CH2:3][CH2:4][S:5](=[O:7])(=[O:6])[NH2:8])[CH:27]=[CH:28][C:23]2=[N:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 136148183-Chloropropane-1-sulfonamideHCID 152710143,6-Dichloroimidazo[1,2-b]pyridazineHCID 23694274Sodium methanolate methanolHCID 86746192Potassium hydrogensulfide ethanol

Produkt 1

HCID 104479033-Chloro-6[(3-sulfamoylpropyl)thio]imidazo[1,2-b]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 1.57 g of 3-chloro-1-propanesulfonamide in 20 ml of methanol was added 20 ml of 2N-potassium hydrogensulfide-ethanol solution, followed by heating at 70° C. for 50 minutes. Then, 1.48 g of 28% sodium methoxide-methanol solution and 1.32 g of 3,6-dichloroimidazo[1,2-b]pyridazine were added to the reaction mixture and refluxed at 100° C. for 3 hours. The mixture was concentrated under reduced pressure, and to the residue was added 20 ml of water, which was adjusted to pH 7.0 with 1N-hydrochloric acid. The precipitated crystals were collected by filtration and recrystallized from methanol and ethyl ether to obtain 1.12 g of the title compound.

Aufarbeitung

  1. temperaturerefluxed at 100° C. for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionto the residue was added 20 ml of water, which
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from methanol and ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-32ffcf5fc18a429fb75b7cdb790bf443
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05202324

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