3-(4-Nitrophenyl)prop-2-enal → (E,E)-2-(Benzylaminocarbonyl)-3-(4-nitrostyryl)acrylonitrile

HRID 392482Notes

Reaction equation

HRID 392482 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][CH:10]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14]([CH2:16][C:17]([N-:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])#[N:15]>>[CH2:20]([NH:19][C:17](/[C:16](=[CH:10]/[CH:9]=[CH:8]/[C:7]1[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)/[C:14]#[N:15])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 156143-(4-Nitrophenyl)prop-2-enalHCID 178511179N-(cyanoacetyl)benzylamide

Product 1

HCID 9858847(E,E)-2-(Benzylaminocarbonyl)-3-(4-nitrostyryl)acrylonitrileYield 82.5%

Procedure

The compound was prepared as described in Example 3 by adding 4-nitrocinnamaldehyde (0.022 g, 0.12 mmol) to N-(cyanoacetyl)benzylamide (Example 4, 0.022 g, 0.12 mmol). After refluxing for 1 h, the product was purified by silica gel chromatography (CHCl3-MeOH, 5:1) to give a yellow solid (0.033 g, 81%) The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 1 h
  3. customthe product was purified by silica gel chromatography (CHCl3-MeOH, 5:1)

Sources & evidence

ORD record
ord-4be7cbb7f1b7495ca26935f24b73548b
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

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