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Potassium Carbonate → 3-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamide

HRID 455160
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HRID 455160 반응식
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]([C:15]([C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=1)[C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH:25]=1)=[O:22])([CH3:17])[CH3:16])#[N:14]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 573868253-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide

생성물 1

HCID 668105993-(1-cyano-1-methylethyl)-N-[3-(2-cyano-4-nitrophenoxy)phenyl]benzamide수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a solution of 3-cyano-4-fluoronitrobenzene (1.76 g, 10.5 mmol) and 3-(1-cyano-1-methylethyl)-N-(3-hydroxyphenyl)benzamide (2.97 g, 10.5 mmol) in N,N-dimethylformamide (20 mL) was added potassium carbonate (2.17 g, 15.7 mmol), and the mixture was stirred at 70° C. for 12 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off, water (100 ml) was added to the filtrate, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, and insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (4.21 g, 94%) as a yellow oil.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. additionwater (100 ml) was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with saturated brine (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate, and insoluble material
  7. filtrationwas filtered off
  8. customThe obtained organic layer was purified by basic silica gel column chromatography (eluate: ethyl acetate)
  9. concentrationthe obtained solution was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0500a04f6eb34a03ae243c3c67125a96
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497274B2

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