Sulfenylation process of pyrozole compound with trifluoromethanesulfonyl radical

A technology of trifluoromethylsulfinyl and sulfinylation, applied in the direction of organic chemistry, etc., can solve the problems of instability, difficult preparation of SOOH, low yield, etc.

Inactive Publication Date: 2002-10-16
JIANGSU PESTICIDE RES INST
View PDF5 Cites 63 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method also has some shortcomings, which are mainly reflected in the reaction raw materials, for example: CF 3 S(O)Cl is extremely unstable, CF 3 S(O)N(CH 3 ) 2 and CF 3 The preparation of SOOH is more difficult, while CF 3 Although S(O)Na is relatively easy to prepare, its reactivity is not high, and the yield is relatively low when carrying out sulfinylation reaction

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a four-neck flask equipped with an electric stirrer, a thermometer, and a reflux condenser, put 23 g of CF 3 SO 2 K (0.12 mol) and 150 ml benzene, add 20 g POCl 3 After reacting for 2 hours, with 32.6 grams (0.1 mol) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole and 33 grams of p-toluenesulfonic acid Dimethylamine salts were mixed, reacted at 40-60°C for 10 hours, and then benzene was distilled off under reduced pressure. Water was added to the resulting solid, filtered, and the filter cake was washed with dichloromethane and dried to obtain a white solid product. The resulting product was identified as 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole, weighing 38.6 grams , determined by HPLC, the content is 90.5%, and the yield is 80%.

Embodiment 2

[0017] In a four-neck flask equipped with an electric stirrer, a thermometer, and a reflux condenser, put CF 3 SO 2 K and CF 3 SO 2 Na mixed salt 22 g (0.12 mol, where CF 3 SO 2 K: CF 3 SO 2 Na=55:45) and 150 milliliters of benzene, add 17 grams of SOCl 2 Carry out the reaction, continue to react for 0.5 hours after no HCl gas escapes, and 32.6 grams (0.1 moles) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) Pyrazole and 33 grams of p-toluenesulfonic acid dimethylamine salt were mixed, and after reacting at 40-60° C. for 10 hours, the post-treatment was carried out according to the method of Example 1. The resulting product was identified as 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole in a yield of 74% .

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 present invention relates to one sulfenylation process of pyrazole compound with CF3SO2K or the mixed salt of CF3SO2K and CF3SO2Na. CF3SO2K or the mixed salt of CF3SO2K and CF3SO2Na are made to react first with reagent A and then with pyrazole compound to obtain pyrazole compound with trifluoromethanesulfonyl radical, where the reagent A is selected from phosgene, TCF, POCl3, PC1 and SOC12. The present invention finds one new sulfenylation reagent, and is easy to prepare, high in reaction, activity, easy to use and high in yield.

Description

technical field [0001] The invention relates to a method for sulfonylation of pyrazole compounds. Background technique [0002] The sulfonylation of pyrazole compounds means that the hydrogen atoms on the carbon atoms of the pyrazole heterocycle are replaced by RSO-groups. There have been some reports on the synthesis methods of these compounds, such as EP0,295,117, EP0,460,940, EP0,484,165, EP1,374,061 and so on. These methods can be roughly divided into two categories. The first category is to prepare the alkylthio compound first and then oxidize it. Usually, RSX (X=Cl or Br) or R-S-S-R reacts with pyrazole compounds, and the reaction product can be oxidized to obtain sulfinyl pyrazoles; the second type is the reaction of sulfinyl compounds with specific compounds and then ring-closing This forms the sulfinylpyrazole. [0003] The above two types of methods are not suitable for industrial production due to the disadvantages of difficult oxidation, high toxicity of react...

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): C07D231/44C07D233/66
Inventor 严传鸣朱新荣俞幼芬
Owner JIANGSU PESTICIDE RES INST
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