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

Preparation method of polysubstituent 1,3,5-triazine

A multi-substitution and substituent technology is applied in the field of preparation of multi-substituted 1,3,5-triazines, which can solve the problems of environmentally unfriendly by-products and achieve the effects of reducing production costs, simple and practical operation, and improving safety

Active Publication Date: 2019-05-28
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the range of substrates is wide, catalysts and oxidants are used in the reaction, and a large number of by-products that are not friendly to the environment are produced

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
  • Preparation method of polysubstituent 1,3,5-triazine
  • Preparation method of polysubstituent 1,3,5-triazine
  • Preparation method of polysubstituent 1,3,5-triazine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), cesium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 96%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

Embodiment 2

[0023]

[0024] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), sodium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 83%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

Embodiment 3

[0026]

[0027] Add 1a (4mmol), sodium difluorochloroacetate (4mmol), potassium carbonate (8mmol) and acetonitrile (10mL) into the reaction flask, then heat the reaction at 120°C for 24 hours. After the reaction was completed, it was first quenched with water, then extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. After concentration, the product 3a was obtained by column chromatography with a mixed solvent of petroleum ether and ethyl acetate. The yield was 78%. Pale yellow solid, Mp: 74-75℃; 1 H NMR (600MHz, CDCl 3 ):δ9.26(s,1H),8.66-8.63(m,4H),7.63-7.59(m,2H),7.57-7.54(m,4H); 13 C NMR (150MHz, CDCl 3 ): δ171.3, 166.7, 135.5, 132.8, 128.9, 128.7.

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 preparation method of polysubstituent 1,3,5-triazine. Specifically, substituen formamidine hydrochloride is used as a reactive substrate, chlorodifluoroacetic acid sodium salt is used as a carbon synthon, and the symmetrical or asymmetrical polysubstituent 1,3,5-triazine is obtained through fracture of carbon-chlorine, carbon-carbon and carbon-fluorine bonds under the action of equivalent inorganic base. The chemical structural general formula of the substituen formamidine hydrochloride is as shown in specification, and the inorganic is one selected from potassium carbonate, sodium carbonate, cesium carbonate. The preparation method disclosed by the invention has the advantages of easily available raw materials, no need for catalyst or oxidant, a wide variety of substrates, simple and convenient operation and environmental friendliness.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted 1,3,5-triazines. Background technique [0002] 1,3,5-Triazine is a very important class of nitrogen-containing heterocyclic compounds, which not only exhibit excellent biological activity, but also can be used as ligands for metal catalysis and organometallic materials. The traditional method generally all is to synthesize 2,4-diphenyl-1,3,5-triazine (Angew.Chem.1960,72,956; Chem.Ber.1963,96,3265; Monatsh.Chem.1995,126,99; Zhurnal Organiccheskoi Khimii,1987,23,2443), however, the substrate range is narrow, the yield is generally low and the reaction conditions are harsh. In recent years, some research groups have used substituted formamidine hydrochloride as substrate, N,N-dimethylformamide, dimethyl sulfoxide, fatty ether, tertiary amine, dichloromethane and other reagents as new carbon synthons , synthesized poly...

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
IPC IPC(8): C07D251/22
Inventor 闫溢哲牛斌张艳艳崔畅李绍青刘延奇史苗苗
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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