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p-Toluenesulfonic acid → 2-acetyl-3-(3-nitrophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

HRID 1700333
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HRID 1700333 반응식
[O:1]=[C:2]([CH3:16])[CH2:3][C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5].[N+:17]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O)([O-:19])=[O:18].N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.O>[C:2]([C:3](=[CH:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=1)[C:4]([NH:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5])(=[O:1])[CH3:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 53935748HCID 53935748, 화합물

생성물 1

HCID 542712132-acetyl-3-(3-nitrophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

시약·촉매·용매 2

HCID 241Benzene용매
HCID 962
Water
용매

실험 절차

1.03 g (4.74 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 723 mg (4.78 mmol) of 3-nitrobenzaldehyde and 0.2 ml (2.02 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 30 ml of benzene overnight while water was removed. Ethyl acetate was added to the reaction mixture. After washing with 2 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate. After the concentration under reduced pressure, the residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

후처리

  1. customwas removed
  2. additionEthyl acetate was added to the reaction mixture
  3. washAfter washing with 2 N hydrochloric acid
  4. dry with materialwith a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter the concentration under reduced pressure
  6. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-b9a5d097f73646caa2d337cffb4ebadb
출처 데이터셋
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06350762B1

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