Imidazo(1,2-b)pyridazine, 6-chloro- → HCID 178527712, compound

HRID 1590053Notes

Reaction equation

HRID 1590053 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C[O-].[Na+].CO.C(O)(=[S:18])C>CO>[SH:18][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 23694274Sodium methanolate methanolHCID 178418634HCID 178418634, compound

Product 1

HCID 178527712HCID 178527712, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

6-Chloroimidazo[1,2-b]pyridazine (13.5 g), 28 W/W % sodium methoxide-methanol solution (17.5 g) and thioacetic acid (7.0 g) were dissolved in 70 ml of methanol and this solution was heated at 150° C. in a sealed tube for 6 hours. The reaction mixture was cooled to room temperature and distilled to remove the organic solvent. The residue was washed three times with chloroform, and the insoluble material was extracted six times with 50 ml of chloroform-methanol (1:1) solution. The combined extracts were distilled to remove the organic solvent. The precipitated crystals were collected by filtration, thereby obtaining 3.7 g of 6-mercaptoimidazo[1,2-b]pyridazine.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationdistilled
  3. customto remove the organic solvent
  4. washThe residue was washed three times with chloroform
  5. extractionthe insoluble material was extracted six times with 50 ml of chloroform-methanol (1:1) solution
  6. distillationThe combined extracts were distilled
  7. customto remove the organic solvent
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-a4ad1f80c5a548d6a64318c367fc63ef
Source dataset
uspto-grants-1993_04
Patent number
US05202324

Reaction notes

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