Ethyl (chloroformyl)acetate → HCID 71744070, compound

HRID 869476Notes

Reaction equation

HRID 869476 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[N:2]=1.Cl[CH:9]([CH:15]=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>CCO>[N:7]1[CH:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:2]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:1]2

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 230373Aminopyridazine

Product 1

HCID 71744070HCID 71744070, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of pyridazin-3-amine (9.51 g, 0.1 mol) and 2-ethyl 2-chloro-3-oxopropanoate (22.5 g, 0.15 mol) in EtOH (20 mL) was stirred at reflux overnight. The mixture was allowed to cool to RT and concentrated in vacuo to remove EtOH. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was separated. The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was slurried in isopropyl ether (50 mL) with stirring for 30 min, collected by filtration and dried in vacuo to afford ethyl imidazo[1,2-b]pyridazine-3-carboxylate (7.8 g, 40.8% yield).

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customto remove EtOH
  4. customThe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  5. customThe organic layer was separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo
  11. stirringwith stirring for 30 min
  12. filtrationcollected by filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-b51482b7c73a4c7b8e49e75b3c7117f5
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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