Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds

An aniline compound and synthesis method technology, which is applied in electrolytic components, electrolytic organic production, electrolytic process and other directions, can solve the problems of long reaction time, lack of application value, low efficiency, etc., and achieves the advantages of short reaction time and green preparation process. Effect

Active Publication Date: 2021-05-28
FUYANG NORMAL UNIVERSITY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the addition of photocatalyst is not recyclable; on the other hand, the reaction time is long, the efficiency is low, and the application value is lacking.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds
  • A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds
  • A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0062] A kind of synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl) aniline compound, comprises the steps:

[0063] Electrocatalytic reaction, electrolyte, isatin compound, benzohydrazide compound, solvent, alkali, respectively, are added to the reaction cell, and catalytic electrodes are installed, and the reaction is stirred with electricity;

[0064] Separation and purification, separation and purification of the solution after the electrocatalytic reaction is completed to obtain 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds; the 2-(5-aryl- 1,3,4-oxadiazol-2-yl)aniline compounds have the structure shown below:

[0065]

[0066] Among them, R 1 for hydrogen, C 1 ~C 5 Alkyl, C 1 ~C 5 One or more of alkoxy and halogen;

[0067] R 2 is phenyl, substituted phenyl, heterocyclyl, and the substituents in the substituted phenyl are trifluoromethyl, halogen, C 1 ~C 5 Alkyl and C 1 ~C 5 of alkoxy.

[0068] Specifically, in a 10mL non-separated electrolytic cell, the...

Embodiment 1

[0074] Example 1: Put isatin (0.3mmol, 44.1mg), benzohydrazide (0.3mmol, 40.8mg), potassium iodide (0.3mmol, 49.8mg), potassium carbonate (0.3mmol , 41.5mg) and dimethyl sulfoxide (3.0mL), the platinum plate electrode was used as both anode and cathode, and reacted under electric stirring (I=10mA) at 120°C. After the reaction was completed (TLC tracking detection), the residue obtained by spinning was used as the eluent to pass the chromatographic column to obtain the product 2-(5-phenyl-1,3,4-oxadiazole- 2-yl) aniline compound with a yield of 77%.

[0075] The 2-(5-phenyl-1,3,4-oxadiazol-2-yl) aniline product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 1~2 , figure 1 For the 2-(5-phenyl-1,3,4-oxadiazol-2-yl) aniline product that the embodiment of the present invention 1 provides 1 H NMR ( 1 H-NMR) spectrogram; figure 2 For the 2-(5-phenyl-1,3,4-oxadiazol-2-yl)aniline product provided in Example 1 of the present invention ...

Embodiment 2

[0079] Example 2: Put isatin (0.3mmol, 44.1mg), 4-methylbenzohydrazide (0.3mmol, 45.1mg), potassium iodide (0.3mmol, 49.8mg), carbonic acid in a 10mL electrolytic cell without separation Potassium (0.3 mmol, 41.5 mg) and dimethyl sulfoxide (3.0 mL) were reacted at 120° C. under electric stirring (I=10 mA), and the platinum plate electrode was used as both the anode and the cathode. After the reaction was completed (TLC tracking detection), the residue obtained by spinning was used as an eluent to pass the chromatographic column to obtain the product 2-(5-(p-methylphenyl)-1,3, 4-oxadiazol-2-yl)aniline compound, the yield was 83%.

[0080] The 2-(5-(p-methylphenyl)-1,3,4-oxadiazol-2-yl) aniline product is analyzed by nuclear magnetic resonance spectrometer, the results can be found in Figure 3-4 , image 3 For the 2-(5-(p-methylphenyl)-1,3,4-oxadiazol-2-yl)aniline product that the embodiment of the present invention 2 provides 1 H NMR ( 1 H-NMR) spectrogram; Figure 4 For...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthetic method of 2-(5-aryl-1,3,4-oxadiazol-2-yl) aniline compound, the method comprises the following steps: electrolyte, substituted isatin, The substituted benzoylhydrazide, solvent, base, and electrode are respectively added to the electrolytic cell without separation, and the electricity is stirred to react; the solution after the reaction is separated and purified to obtain 2-(5-aryl-1,3,4-oxadi Azol-2-yl) aniline compounds, the preparation process does not require the use of metals and chemical oxidants, the reaction time is short, and the preparation process is green and environmentally friendly.

Description

technical field [0001] The invention relates to the technical field of synthesis of aniline compounds, in particular to a synthesis method of 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds. Background technique [0002] 2,5-Diaryl-1,3,4-oxadiazoles are an important class of oxygen-containing heterocycles, which widely exist in bioactive molecules and optoelectronic materials. In particular, 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds, due to the presence of amino groups in their molecules, provide the possibility for further conversion into useful organic molecules. Therefore, its synthesis has always been the research focus of organic chemists. However, due to the compatibility of amino groups in the system, there are few reports on 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds. [0003] In 2015, Wu's group synthesized 2-(5-aryl-1,3,4-oxadiazol-2-yl)aniline compounds (C . Xu, F-C. Jia, Q. Cai, D-K. Li, Z-W. Zhou and A-X. Wu, Chem. Commun, 2015, 51, 6629.). Alt...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/05C25B3/23
CPCC25B3/00
Inventor 钱朋沈毅银
Owner FUYANG NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com