Ethyl (chloroformyl)acetate → Ethyl imidazo[1,2-B]pyridazine-3-carboxylate

HRID 869476ノート

反応式

HRID 869476 の反応式
[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

参加物

4

反応物 2

HCID 118030Ethyl (chloroformyl)acetateHCID 230373Aminopyridazine

生成物 1

HCID 71744070Ethyl imidazo[1,2-B]pyridazine-3-carboxylate収率 40.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b51482b7c73a4c7b8e49e75b3c7117f5
出典データセット
uspto-grants-2015_03
特許番号
US08969363B2

反応ノート

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