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

HRID 465945

Reaction equation

HRID 465945 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[SH2:9].[K].C[O-].[Na+].CO.[Cl:16][C:17]1[N:18]=[C:19]2[CH:24]=[CH:23][C:22](Cl)=[N:21][N:20]2[CH:26]=1>CO>[Cl:16][C:17]1[N:18]=[C:19]2[CH:24]=[CH:23][C:22]([S:9][CH2:2][CH2:3][CH2:4][S:5](=[O:7])(=[O:6])[NH2:8])=[N:21][N:20]2[CH:26]=1

Participants

6

Reactant 4

HCID 136148183-Chloropropane-1-sulfonamideHCID 144223582,6-Dichloroimidazo[1,2-b]pyridazineHCID 23694274Sodium methanolate methanolHCID 86743134Potassium hydrogensulfide

Product 1

HCID 198151402-Chloro-6-[(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 20 ml of 2N-potassium hydrogensulfide, followed by heating at 70° C. for 50 minutes. Further, 1.48 g of 28% sodium methoxide-methanol solution and 1.32 g of 2,6-dichloroimidazo[1,2-b]pyridazine [Japanese Unexamined Patent Publication No. SHO 64(1989)-38092] were added to the reaction mixture, and refluxed at 100° C. for 3 hours. The mixture was concentrated under reduced pressure. Then, the residue to which was 20 ml of water was added was adjusted to pH 7.0 with 1N-hydrochloric acid. The precipitated crystals were collected by filtration and subjected to a silica gel column chromatography, eluting with chloroform and methanol (50:1). The corresponding combined fractions were concentrated, and the residue was recrystallized to obtain 1.1 g of the title compound.

Workup

  1. temperaturerefluxed at 100° C. for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionwas added
  4. filtrationThe precipitated crystals were collected by filtration
  5. washeluting with chloroform and methanol (50:1)
  6. concentrationThe corresponding combined fractions were concentrated
  7. customthe residue was recrystallized

Sources & evidence

ORD record
ord-2a3ea9a28a2049fe9abe521e22d57ba9
Source dataset
uspto-grants-1992_10
Patent number
US05155108

Linked notes

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