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Benzyl Bromide → 1-benzyl-3-chloro-5-methoxypyridazin-4(1H)-one

HRID 1747799
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반응식

HRID 1747799 반응식
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([N:4]1[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([Cl:1])=[N:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
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참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178493809HCID 178493809, 화합물

생성물 1

HCID 866865601-benzyl-3-chloro-5-methoxypyridazin-4(1H)-one수율 126.8%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매
HCID 6228
Dimethylformamide
용매

실험 절차

3-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in DMF (300 mL), NaH (3.26 g, 55 wt %) and tetrabutylammoniumiodide (4.60 g) were added at 0° C., and the mixture was stirred at the same temperature for 10 min. To the reaction mixture was added benzylbromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, extracted with dichloromethane, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and recrystallized from ethyl acetate/hexane to give the title compound (19.8 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionextracted with dichloromethane
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-24469635a0c54183a29e172b71aa934f
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150588B2

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