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

Method for synthesizing 1,2,4-benzothiadiazine series compounds in aqueous solution

A technology of benzothiadiazines and compounds, which is applied in the field of preparation of 1,2,4-benzothiadiazines compounds, can solve the problems of increased production costs and high equipment requirements, and achieves extremely easy acquisition and high product yield The effect of high and good application prospects

Active Publication Date: 2019-09-06
JIANGXI NORMAL UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a potential problem in this method is that the cobalt catalyst will decompose and release a small amount of toxic gas carbon monoxide during the reaction, and the reaction also needs to use silver salt as a co-catalyst. In addition, the compound 3-aryl (alkyl) base-1,4, 2-Oxadiazol-5-one needs to be additionally prepared as a reaction raw material, and halogenated hydrocarbon trichloromethane is used as an organic solvent in the reaction. These factors will lead to high requirements for equipment and increased production during large-scale preparation. Potential issues with cost

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
  • Method for synthesizing 1,2,4-benzothiadiazine series compounds in aqueous solution
  • Method for synthesizing 1,2,4-benzothiadiazine series compounds in aqueous solution
  • Method for synthesizing 1,2,4-benzothiadiazine series compounds in aqueous solution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Under air atmosphere, the catalyst cuprous oxide (2.1mg, 0.015mmol) and 2-bromophenylmethyl iminosulfone (70.4mg, 0.3mmol) and tetrabutylammonium iodide (11.0mg, 0.03mmol) and benzaldehyde (41.4mg, 0.39mmol) was dissolved in water (1mL), then added sodium azide (39.0mg, 0.6mmol) sealed, placed in 90 ° C environment for 12 hours, TLC detection of complete reaction, cooled to room temperature, added water (2mL), then added saturated potassium carbonate solution (2mL) and stirred for 10 minutes, extracted 4 times with ethyl acetate, combined the organic phases and dried with anhydrous sodium sulfate, the pure product 3a separated by flash column chromatography, productive rate 95% . The following is the NMR experimental data of product 3a:

[0033] 1 H NMR (400MHz, CDCl 3 )δ: 8.38(d, J=7.2Hz, 2H), 7.80(d, J=8.0Hz, 1H), 7.69(t, J=7.6Hz, 1H), 7.62(d, J=8.0Hz, 1H) ,7.45(d,J=6.4Hz,3H),7.38(t,J=7.4Hz,1H),3.52(s,3H).

[0034] 13 C NMR (100MHz, CDCl 3 )δ: 157.9...

Embodiment 2

[0036]

[0037] Catalyst cuprous oxide (2.1g, 15mmol) and 2-bromophenylmethyl iminosulfone (70.4g, 0.3mol) and tetrabutylammonium iodide (11.0g, 0.03mol) and benzaldehyde ( 41.4g, 0.39mol) was dissolved in water (1L), then added sodium azide (39.0g, 0.6mol) to seal, and placed in an environment of 90 ° C for 12 hours, TLC detected that the reaction was complete, cooled to room temperature, added water ( 2L), then add saturated potassium carbonate solution (2L) and stir for 10 minutes, then extract 4 times with ethyl acetate, combine the organic phases and dry with anhydrous sodium sulfate, the pure product 3a separated by flash column chromatography, the yield is 90%.

Embodiment 3

[0039]

[0040] Catalyst cuprous oxide (2.1g, 15mmol) and 2-bromophenylmethyl iminosulfone (70.4g, 0.3mol) and tetrabutylammonium bromide (7.9g, 0.03mol) and benzaldehyde ( 41.4g, 0.39mol) was dissolved in water (1L), then methanesulfonyl azide (72.6g, 0.6mol) was added to seal it, and then placed in an environment of 90°C for 12 hours, TLC detected that the reaction was complete, cooled to room temperature, and added water (2L), then add saturated potassium carbonate solution (2L) and stir for 10 minutes, then extract 4 times with ethyl acetate, combine the organic phases and dry with anhydrous sodium sulfate, the pure product 3a separated by flash column chromatography, productive rate 90% .

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 provides a preparation method of 1,2,4-benzothiadiazine-1-oxide series compounds. The method adopts a one-pot reaction, uses commercially available 2-bromophenylimino sulfone and aromatic (alkyl) aldehyde as reaction substrates, uses stable, cheap and nontoxic copper oxide as a catalyst, uses water as a green and pollution-free solvent, and reacts for 12 to 15 hours in an air environment at 80 to 100 DEG C to synthesize 1,2,4-benzothiadiazine series compounds. According to the invention, water is taken as a solvent, so that the environment is basically free from pollution, alkaliand inert gas protection are not required, no special requirements are imposed on reaction equipment, and the operation is simple and convenient; and the one-pot reaction is adopted, so that the operation of preparing and separating intermediates is omitted, and therefore the synthesis cost is extremely low. The product obtained by the method has excellent chemical selectivity, high production efficiency, wide compatibility of substrate functional groups, accords with the characteristics of green reaction, is suitable for large-scale preparation, has extremely excellent industrial applicationprospect, and is an environment-friendly green chemical technology.

Description

technical field [0001] The invention relates to a derivative of a sulfur-containing and diazaheterocyclic drug skeleton, in particular to a preparation method of 1,2,4-benzothiadiazine compounds. Background technique [0002] Sulfone imino derivatives have important physiological and pharmacological activities. At present, the marketed drugs containing the sulfoimino skeleton structure, that is, the structure containing sulfur-oxygen and sulfur-nitrogen double bonds include: Suloxifen (Suloxifen) for the treatment of asthma, HE-HK 52 for spasm relief, Sulfoxaflor (Sulfoxaflor) for insect repellent, Sudexanox (Sudexanox) for anti-allergy, pan-CDK (ZK 304709) for inhibiting cyclin (CDKs) activating enzymes, and inhibiting lymphocytes NSC 287474 for HIV Reverse Transcriptase and others. [0003] Among the iminosulfone series derivatives, the benzo[e][1,2,4]thiadiazole-1-oxyl derivatives with a phenyl ring structure are more important heterocyclic skeleton structures. Compoun...

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): C07D285/24C07D417/04
CPCC07D285/24C07D417/04
Inventor 陈知远吴翠
Owner JIANGXI NORMAL 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