Benzyl Bromide → 2-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one

HRID 446890

반응식

HRID 446890 반응식
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[Cl:8].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:4]1[C:3](=[O:9])[C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=[N:5]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 732474,5-Dichloro-3-hydroxypyridazine

생성물 1

HCID 7224382-Benzyl-4,5-dichloro-2,3-dihydropyridazin-3-one수율 88%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a mixture of 4,5-dichloro-2H-pyridazin-3-one (3.3 g, 20.0 mmol) and Cs2CO3 (9.77 mg, 1.5 eq) were added DMF (15 mL) and benzyl bromide (3.10 mL, 1.3 eq), which was then stirred for 3 h at 60° C. under nitrogen atmosphere. The mixture was concentrated under reduced pressure, and the residue was extracted twice with ethyl acetate (200 mL). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (NaHCO3, 100 mL×2) and aqueous sodium chloride solution, dried (anhydrous Na2SO4), and concentrated under reduced pressure. The residue was separated by column chromatography (10% ethyl acetate-hexane) to give 4.48 g (88%) of the title compound.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted twice with ethyl acetate (200 mL)
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (NaHCO3, 100 mL×2) and aqueous sodium chloride solution
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (10% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-9b94d4afb4674eb596256d10c129bba0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481537B2

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