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

N- trifluoromethoxy pyridine salt compound and preparation method and use thereof

A compound and alkoxy technology, which is applied in ether preparation, organic chemistry, etc., can solve problems such as the lack of methods for trifluoromethoxylation reaction, harsh reaction conditions, and complicated steps of trifluoromethoxylation reaction

Active Publication Date: 2015-11-04
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The technical problem to be solved by the present invention is to overcome the defects in the prior art that the steps of the trifluoromethoxylation reaction are complicated, the reaction conditions are harsh, the applicable substrates are limited, and the method for directly realizing the trifluoromethoxylation reaction in one step is lacking, etc., Provided are N-trifluoromethoxypyridinium salt compounds and their preparation methods and uses

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
  • N- trifluoromethoxy pyridine salt compound and preparation method and use thereof
  • N- trifluoromethoxy pyridine salt compound and preparation method and use thereof
  • N- trifluoromethoxy pyridine salt compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Synthesis of N-trifluoromethoxy-2,6-dichloropyridine hexafluoroantimonate

[0063]

[0064] Under a nitrogen atmosphere, the compound 2-(trifluoromethoxy)biphenyl-2'-hexafluoroantimonate diazonium salt (3.63g, 7.26mmol) was added to a 100mL sealed tube, and 30mL of dichloromethane was added, 2,6 - Dichloropyridine nitroxide (2.38 g, 14.5 mmol), 3.5 hours at 42°C. The solid was precipitated by cooling, part of the solvent was evaporated under reduced pressure, allowed to stand, and filtered to obtain 1.73 g of a white solid with a yield of 51% and a nuclear magnetic purity greater than 97%. Further purification was obtained by recrystallization from THF / anhydrous ether. white solid. The melting point is 205-207°C. Infrared characterization (potassium bromide film): 3101, 1583, 1557, 1477, 1460, 1310, 1257, 1180, 1106, 904, 831, 780, 658cm -1 .NMR spectrum: 1 H NMR characterization (300MHz, CD 3 CN, 23℃, δ): 8.67(t, J=8.5Hz, 1H), 8.35(d, J=8.4Hz, 2H). 19 F nucle...

Embodiment 2

[0066] Synthesis of N-trifluoromethoxy-2,4,6-trichloropyridine hexafluoroantimonate

[0067]

[0068] Under a nitrogen atmosphere, add the compound 2-(trifluoromethoxy)biphenyl-2'-hexafluoroantimonate diazonium salt (1.25g, 2.5mmol) into a 25mL sealed tube, add 10mL of dichloromethane, 2,4 , 6-trichloropyridine nitroxide (496mg, 2.5mmol), at 42°C for 3 hours. The solid was precipitated by cooling, and part of the solvent was evaporated under reduced pressure, allowed to stand, and filtered to obtain 719 mg of a white solid with a yield of 57% and a nuclear magnetic purity greater than 97%. Further purification was obtained by recrystallization from THF / anhydrous ether. white solid. Melting point: 194-195°C. Infrared characterization (potassium bromide film): 3078, 1582, 1537, 1421, 1395, 1308, 1263, 1115, 876, 860, 793, 660cm -1 .NMR spectrum: 1 H NMR characterization (300MHz, CD 3 CN,23℃,δ):8.37(s). 19 F nuclear magnetic characterization (375MHz, CD 3 CN,23℃,δ):-59...

Embodiment 3

[0070] Synthesis of N-trifluoromethoxy-2,3,4,5,6-pentachloropyridine hexafluoroantimonate

[0071]

[0072] Under a nitrogen atmosphere, add the compound 2-(trifluoromethoxy)biphenyl-2'-hexafluoroantimonate diazonium salt (1.25g, 2.50mmol) into a 100mL sealed tube, add 10mL of dichloromethane, 2,3 , 4,5,6-pentachloropyridine nitroxide (668mg, 2.5mmol), at 42°C for 3.5 hours. The solid was precipitated by cooling, and part of the solvent was evaporated under reduced pressure, allowed to stand, and filtered to obtain 670 mg of a white solid with a yield of 47% and a nuclear magnetic purity greater than 97%. Further purification was obtained by recrystallization from THF / anhydrous ether. white solid. Infrared characterization (potassium bromide film): 1382, 1331, 1313, 1173, 1011, 765, 740cm -1 .NMR spectrum: 19 F nuclear magnetic characterization (375MHz, CD 3 CN,23℃,δ):-58.31(s),-111.01to-136.96(m).

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 discloses a N- trifluoromethoxy pyridine salt compound and a preparation method and use thereof. The preparation method of the N- trifluoromethoxy pyridine salt compound as shown in formula I comprises the following steps: under gas protection, in an organic solvent, under light or no light conditions, the compound as shown in the formula I is prepared by reaction as shown in the specification of a compound as shown in formula III and a compound as shown in formula II. The present invention also discloses use in trifluoromethoxylation reaction of the compound as shown in the formula I and an electron-rich system compound. The N- trifluoromethoxy pyridine salt compound has high reactivity, can be used to direct pro-electric trifluoromethoxylation reaction, is mild in reaction conditions, simple in operation and after-treatment, suitable for industrial production, simple in synthesis method, easily available in raw materials, and suitable for commercialization.

Description

technical field [0001] The present invention relates to N-trifluoromethoxypyridinium salt compounds, their preparation method and application. Background technique [0002] Due to the unique structural characteristics of fluorine atoms (small atomic radius, large electronegativity and strong carbon-fluorine bond), the introduction of fluorine atoms can greatly change the polarity, fat solubility and biological activity of compounds. It has become a hotspot in life science research (Jones, C.J.d-and f-block chemistry, RSC, 2001.). Of all the groups studied, trifluoromethoxy substitution is effective in enhancing the bioactivity of the molecule, but this is probably the least studied group, described as the "least familiar" fluorine-containing group ( Leroux, F.R.; Manteau, B.; Vors, J.P.; Pazenok, S. Beilstein J. Org. Chem. 2008, 4, 13.). In addition to trifluoromethoxy-containing liquid crystal materials (Leroux, F.R.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827.)...

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): C07D213/89C07C41/01C07C43/225
CPCC07C41/01C07C43/225C07D213/89
Inventor 梅本照雄周敏胡金波
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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