Ethyl 2-chloroacetoacetate → Ethyl 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxylate

HRID 1067598노트

반응식

HRID 1067598 반응식
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl[CH:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:16]([CH3:17])[N:1]=2)[N:4]=1

참가 물질

4

반응물 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 216436-Amino-3-chloropyridazine

생성물 1

HCID 14091884Ethyl 6-chloro-2-methylimidazo[1,2-b]pyridazine-3-carboxylate수율 12.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

12.9 g of 3-amino-6-chloropyridazine was suspended in 250 ml of ethanol; 18.1 g of ethyl 2-chloro-3-oxobutanoate was added, followed by thermal refluxing for 6 hours. After cooling, the mixture was concentrated under reduced pressure; the residue was ajusted to pH 7 by the addition of aqueous sodium bicarbonate; ethyl ether was added; the precipitated was collected by filtration and extracted with ethyl ether; the extract was washed with saturated saline and dried with magnesium sulfate. The dry product was concentrated under reduced pressure; ethanol-1 N aqueous solution of sodium hydroxide (1:1) was added; the crystal precipitated was collected by filtration; the filtrate was concentrated again. The residue was crystallized by the addition of ethyl acetate and collected by filtration to yield 3.09 g of the title compound.

후처리

  1. customrefluxing for 6 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionthe residue was ajusted to pH 7 by the addition of aqueous sodium bicarbonate
  5. additionethyl ether was added
  6. filtrationthe precipitated was collected by filtration
  7. extractionextracted with ethyl ether
  8. washthe extract was washed with saturated saline
  9. dry with materialdried with magnesium sulfate
  10. concentrationThe dry product was concentrated under reduced pressure
  11. additionethanol-1 N aqueous solution of sodium hydroxide (1:1) was added
  12. customthe crystal precipitated
  13. filtrationwas collected by filtration
  14. concentrationthe filtrate was concentrated again
  15. customThe residue was crystallized by the addition of ethyl acetate
  16. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-00889c66e5854662b5802d157ae14b44
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248740B1

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