Isopropylamine → 2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide

HRID 17884

반응식

HRID 17884 반응식
C(O[C:4](=[O:22])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)=[O:7])C.[CH:23]([NH2:26])([CH3:25])[CH3:24]>C1(C)C=CC=C(C)C=1>[CH2:15]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[C:6]([C:5](=[CH:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([NH:26][CH:23]([CH3:25])[CH3:24])=[O:22])=[O:7])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

4

반응물 2

HCID 6363IsopropylamineHCID 10334847Ethyl 3-[3-(benzyloxy)phenyl]-3-oxopropanoate

생성물 1

HCID 866140272-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide수율 108.9%

시약·촉매·용매 1

HCID 7929M-Xylene용매

반응 조건

온도
150 °C

실험 절차

3-(3-Benzyloxyphenyl)-3-oxopropionate ethyl ester (174.42 g, 584.47 mmol) was dissolved in m-xylene and the reaction mixture was refluxed while stirring for 30 min at 150° C. Then, isopropylamine (38 g, 642.92 mmol) was added dropwise to the mixture. After stirring and refluxing for 24 hours at room temperature, the organic layer was extracted with saturated sodium chloride and ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain 2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide (127.13 g, yield 70%) as yellow oil.

후처리

  1. temperaturethe reaction mixture was refluxed
  2. stirringAfter stirring
  3. temperaturerefluxing for 24 hours at room temperature
  4. extractionthe organic layer was extracted with saturated sodium chloride and ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customresulting residue
  8. customwas purified by column chromatography (ethyl acetate:hexane=1:2)

출처 및 근거

ORD 기록
ord-6f30f4c684614fd5b1c8d02605a5658c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741323B2

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