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

HRID 465944

Reaction equation

HRID 465944 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5d531bf8726249378baa5fe29c51d349
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Linked notes

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