2-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)- → (E,E)-2-Aminothiocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrile

HRID 392479Notes

Reaction equation

HRID 392479 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:14][CH3:15])[C:12]=1[OH:13])[CH:6]=[CH:7][CH:8]=O.[C:16]([CH2:18][C:19]([NH2:21])=[S:20])#[N:17]>>[NH2:21][C:19](/[C:18](=[CH:8]/[CH:7]=[CH:6]/[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]([OH:13])=[C:11]([O:14][CH3:15])[CH:10]=1)/[C:16]#[N:17])=[S:20]

Participants

3

Reactant 2

HCID 1192162-Propenal, 3-(4-hydroxy-3,5-dimethoxyphenyl)-HCID 14162772-Cyanoethanethioamide

Product 1

HCID 135506539(E,E)-2-Aminothiocarbonyl-3-(3,5-dimethoxy-4-hydroxystyryl)acrylonitrileYield 52%

Procedure

The compound was prepared as described in Example 3 by adding 3,5-dimethoxy-4-hydroxycinnamaldehyde (0.15 g, 0.72 mmol) to 2-cyanothioacetamide (0.073 g, 0.72 mmol). After refluxing for 1 h the residue was purified on a TLC-plate in hexane-ethyl acetate, 1:1 to give a red solid (0.10 g, 52%). The product gave the following analytical data:

Workup

  1. customThe compound was prepared
  2. temperatureAfter refluxing for 1 h the residue
  3. customwas purified on a TLC-plate in hexane-ethyl acetate, 1:1

Sources & evidence

ORD record
ord-7a4acea16670428d93f0e174c7e67310
Source dataset
uspto-grants-2004_10
Patent number
US06800659B2

Reaction notes

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