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

HRID 1700333
ノート
印刷プレビュー

反応式

HRID 1700333 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 53935748HCID 53935748、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒
HCID 962
Water
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b9a5d097f73646caa2d337cffb4ebadb
出典データセット
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06350762B1

反応ノート

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