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

HRID 465944

Reaktionsgleichung

Reaktionsgleichung von HRID 465944
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 20ml 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 1.32g 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-5d531bf8726249378baa5fe29c51d349
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155108

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