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

HRID 1700333Notes

Reaction equation

HRID 1700333 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b9a5d097f73646caa2d337cffb4ebadb
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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