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

2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione, derivatives and synthesis method thereof

A thiadiazole and disubstitution technology, applied in 2, can solve the problems of complex synthesis steps and poor atom economy, and achieve the effect of simple reaction system, mild reaction conditions, and high atom economy

Pending Publication Date: 2019-09-06
XIANGTAN UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the methods for synthesizing such compounds have complicated synthetic steps and poor atom economy, often requiring pre-functionalization of starting materials

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
  • 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione, derivatives and synthesis method thereof
  • 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione, derivatives and synthesis method thereof
  • 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione, derivatives and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0037] Step 1: add oxime lipid compound (see Table 1 for specific substance) and phenylisothiocyanate compound (see Table 1 for specific substance) in the reaction vessel, respectively add elemental sulfur (see Table 1 for specific substance), alkali ( Specific substances are shown in Table 1) and organic solvents (see Table 1 for specific substances) are added in the reaction vessel.

[0038] Step 2: the reaction vessel is evenly heated (as oil bath heating) to the temperature described in Table 1, and the oxime lipid compound and phenylisothiocyanate compound are reacted in a solvent, and continue the process described in Table 1 Time; the reaction atmosphere that needs to be explained is oxygen reaction.

[0039] Step 3: Purification step.

[0040] Table 1: Oxime lipid compound and phenyl isothiocyanate compound, elemental sulfur, alkali, organic solvent, (oxime lipid compound, phenylisothiocyanate compound, elemental sulfur and alkali in embodiment 1-10 ) molar ratio, re...

Embodiment 4

[0045] The nuclear magnetic data of embodiment 4 product is as follows:

[0046] 1 H NMR (400MHz, Chloroform-d) δ8.19-8.13(m, 2H), 7.51-7.44(m, 4H), 7.25-7.20(m, 1H), 7.17(dd, J=8.4, 1.2Hz, 2H ), 1.36(s, 9H); 13 C NMR (100MHz, Chloroform-d) δ165.8, 159.2, 153.7, 153.3, 129.9, 129.9, 128.8, 125.6, 125.2, 119.0, 34.9, 31.2.

Embodiment 6

[0047] The nuclear magnetic data of embodiment 6 product is as follows:

[0048] 1 H NMR (400MHz, Chloroform-d) δ8.17-8.12 (m, 2H), 7.62-7.57 (m, 2H), 7.50-7.44 (m, 2H), 7.26-7.22 (m, 1H), 7.16 (dd , J=8.4, 1.1Hz, 2H); 13 C NMR (100MHz, Chloroform-d) δ 165.0, 158.1, 152.9, 131.5, 131.4, 130.6, 129.9, 125.9, 125.0, 119.0.

[0049] Conversion rate and product of table 2 embodiment 1-10 reaction

[0050]

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 mainly relates to a synthesis method of 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione and derivatives thereof. The 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thione and the derivatives thereof are prepared from oxime lipid compounds, phenyl isothiocyanate compounds and elemental sulfur by a one-pot method under the promotion of an alkali in an oxygen atmosphere. The product withstable molecular structure and excellent chemical properties and the additional products thereof are prepared. The method does not need transition metal catalysis, and provides a new path for the synthesis of the 2,5-disubstituted-1,2,4 thiadiazole-3 (2H)-thioketone compounds. The method has the characteristics of simple reaction system, mild reaction conditions, less reaction equipment, simple and convenient experimental operation, medium and partial yield and the like.

Description

technical field [0001] The invention relates to 2,5-disubstituted-1,2,4thiadiazole-3(2H)-thione, derivatives and a synthesis method thereof, belonging to the field of organic synthesis. Background technique [0002] 2,5-disubstituted-1,2,4thiadiazole-3(2H)-thione and its derivatives can be used as intermediates in various organic synthesis, analytical reagents, fuel additives, lubricant additives, and other pharmaceutical compounds , Mineral flotation collectors, raw materials for flash rust and corrosion inhibitors in paints. So far, the methods for synthesizing such compounds have complicated synthetic steps and poor atom economy, and often require pre-functionalization of starting materials. Contents of the invention [0003] Accordingly, the object of the present invention is to provide a 2,5-disubstituted-1,2,4thiadiazole-3(2H)-thione and its derivatives. [0004] Another object of the present invention is to provide a synthetic method of 2,5-disubstituted-1,2,4thia...

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): C07D285/08
CPCC07D285/08
Inventor 黄华文屈中华邓国军肖福红陈善平
Owner XIANGTAN UNIV
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