Sulfuric Acid → HCID 22989226, compound

HRID 1169146Notes

Reaction equation

HRID 1169146 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([CH3:22])([CH3:21])[C:17](OC)=[O:18])[N:15]=2)[N:12]=1.[CH:23]([OH:26])([CH3:25])[CH3:24]>>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([C:16]([CH3:22])([CH3:21])[C:17]([O:26][CH:23]([CH3:25])[CH3:24])=[O:18])[N:15]=2)[N:12]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 11075988HCID 11075988, compound

Product 1

HCID 22989226HCID 22989226, compound

Procedure

In 18 ml of isopropanol, 995 mg of concentrated sulfuric acid was dissolved; 1.0 g of methyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate was added, followed by thermal refluxing for 40 hours. After cooling, the mixture was concentrated under reduced pressure, neutralized by the addition of aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated saline, dried over magnesium sulfate and concentrated under reduced pressure; the crystal precipitated was collected, washed with hexane and dried to yield 794 mg of the title compound. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane:ethyl acetate (5:1). The desired fraction was collected and dried to yield 215 mg of the title compound.

Workup

  1. customrefluxing for 40 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionneutralized by the addition of aqueous sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated saline
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe crystal precipitated
  10. customwas collected
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-9903e59fd99b4121bd177a396315dd68
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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