Water → Ethyl 2-(3,6-dichloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate

HRID 1067597Notes

Reaction equation

HRID 1067597 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:10]=2)[N:7]=1.[Cl:19]N1C(=O)CCC1=O.O>C(OCC)(=O)C>[Cl:19][C:8]1[N:6]2[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]([CH3:17])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 11043751Ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoate

Product 1

HCID 22989216Ethyl 2-(3,6-dichloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionateYield 97.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.07 g of ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionate was suspended in 60 ml of ethyl acetate; 2.13 g of N-chlorosuccinimide was added, followed by thermal refluxing for 4 hours. After cooling, water was added, followed by extraction with ethyl acetate; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product 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 concentrated under reduced pressure to yield 4.48 g of the title compound.

Workup

  1. customrefluxing for 4 hours
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe extract was washed with saturated saline
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe dry product was concentrated under reduced pressure
  7. washeluted with hexane:ethyl acetate (5:1)
  8. customThe desired fraction was collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af83afebb6d5400cbd2686ba8a0a1beb
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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