M-aminophenylacetylene preparation method

The technology of an aminophenylacetylene and a synthesis method, which is applied in the synthesis field of m-aminophenylacetylene, can solve the problems of unsuitable industrial production, difficult control of reaction conditions and high product cost, and achieves the advantages of less environmental pollution, lower production cost and cost saving. Effect

Inactive Publication Date: 2018-09-25
XIAN GERUIDE NEW CHEM MATERIALS CO LTD
View PDF6 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are easy to get, and there are five steps of reaction, but the reaction conditions of the selective debromination process are difficult to control, a large amount of reaction by-products will be produced, and the yield is as low as 45%, resulting in higher product cost, so it is not suitable for industrial production

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
  • M-aminophenylacetylene preparation method
  • M-aminophenylacetylene preparation method
  • M-aminophenylacetylene preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]Preparation of dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent). Add 33.2g (0.2mol) of dimethyl acetonyl phosphate and 300ml toluene in sequence in a 1000ml reaction flask, add 5.1g (0.21mol) of NaH in batches, and after all the gas is released, p-toluenesulfonyl azide A mixture of 41.4g (0.21mol) and 500ml of tetrahydrofuran was added to the reaction solution, and the reaction was carried out at room temperature for 16h. After the reaction, add petroleum ether to dilute, filter, wash the filter cake with ether, evaporate the solvent under reduced pressure to obtain 33.1 g of yellow liquid with a yield of 86.5%.

Embodiment 2

[0038] Preparation of dimethyl (1-diazo-2-oxopropyl)phosphonate (Bestmann-Ohira reagent). Add 33.2 g (0.2 mol) of dimethyl acetonyl phosphate and 300 ml tetrahydrofuran in sequence in a 1000 ml reaction flask, add 8 g (0.2 mol) of sodium hydride in batches, and after all the gas is released, p-toluenesulfonyl azide A mixture of 47.3g (0.24mol) and 500ml of tetrahydrofuran was added to the reaction solution, and reacted at room temperature for 12h. After the reaction, dilute with petroleum ether, filter, wash the filter cake with ether, evaporate the solvent under reduced pressure to obtain 33.7 g of yellow liquid with a yield of 88%.

Embodiment 3

[0040] Preparation of m-nitrophenylacetylene. Add m-nitrobenzaldehyde 15.1g (0.1mol) and homemade (1-diazo-2-oxopropyl)phosphonic acid dimethyl ester (Bestmann-Ohira reagent) 18.3g in a dry and clean 1000ml reaction flask (0.11mol) (purified) and 750ml of methanol, cooled to 0-5°C, slowly added 20.7g (0.15mol) of anhydrous potassium carbonate, the temperature was controlled at 0-5°C when adding, after the addition, keep stirring for 2h. Then the reaction temperature was raised to room temperature, and the stirring reaction was continued for 8h. Stop the reaction, add saturated ammonium chloride aqueous solution, dichloromethane 150ml×3 extract, combine the organic phases, and dry over anhydrous sodium sulfate for 2h. Filter, wash the filter cake with an appropriate amount of dichloromethane, combine the organic phases, concentrate under reduced pressure to recover the solvent, freeze and solidify to obtain 13.1 g of a light yellow solid, with a yield of 89.2%.

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 an m-aminophenylacetylene preparation method, which comprises: carrying out a reaction on dimethyl acetylmethylphosphonate and tosyl azide under a strong alkali condition to obtain dimethyl(1-diazo-2-oxopropyl)phosphonate; carrying out a reaction on the dimethyl(1-diazo-2-oxopropyl)phosphonate and m-nitrobenzaldehyde under an alkaline catalyst condition to obtain m-nitrophenylacetylene; and reducing the m-nitrophenylacetylene to obtain the m-aminophenylacetylene. According to the present invention, the easily-available raw material m-nitrobenzaldehyde is used so as to avoid the use of the expensive raw materials such as m-iodonitrobenzene, m-bromonitrobenzene or m-nitrophenylacetylene and reduce the production cost; and the synthesis method has advantages of simpleoperation, no requirement of high pressure equipment, no requirement of vacuum rectification, simple requirement on equipment, cost saving and low environment pollution, and is suitable for industrialproduction.

Description

technical field [0001] The invention relates to a synthesis method of m-aminophenylacetylene, belonging to the fields of organic chemistry and medicinal chemistry. Background technique [0002] m-Aminophenylacetylene, also known as 3-ethynylaniline, has two functional groups, amino and alkynyl, and can derive a series of important intermediates. The structural formula is: [0003] [0004] m-aminophenylacetylene itself has good mechanical properties and high mechanical strength, can withstand quite high torsional shear force, and has very good high temperature resistance and wear resistance. It reacts with maleic anhydride to form polyimides The compound is extremely important. The resin made of this polymer has high thermal stability and high mechanical strength. It is a high-grade resin used in the synthesis of aviation, aerospace, military and other fields, and can be applied to the empennage of aircraft And the shell of the missile; m-aminophenylacetylene and quinaz...

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 Applications(China)
IPC IPC(8): C07C209/36C07C211/45
CPCC07C209/36C07C201/12C07F9/4006C07C205/06C07C211/45
Inventor 孙蓓林泽欣
Owner XIAN GERUIDE NEW CHEM MATERIALS CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap