Sulfuric Acid → HCID 22989226, compound
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]=1Participants
Procedure
In 18 ml of isopropanol, 995 mg of concentrated sulfuric acid was dissolved; 1.0 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 and dried with magnesium sulfate. The dry product was 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
- customrefluxing for 40 hours
- temperatureAfter cooling
- concentrationthe mixture was concentrated under reduced pressure
- additionneutralized by the addition of aqueous sodium bicarbonate
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated saline
- dry with materialdried with magnesium sulfate
- concentrationThe dry product was concentrated under reduced pressure
- customthe crystal precipitated
- customwas collected
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-12b1a71a557147309303faa54580e7cd
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06248740B1
Reaction notes
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