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

A kind of alkyl trifluoromethyl sulfide compound and preparation method thereof

A technology of alkyl trifluoromethyl sulfide and trifluoromethyl sulfide, which is applied in the field of alkyl trifluoromethyl sulfide compounds and their preparation, and can solve the problem that trifluoromethyl sulfide reagents are difficult to obtain and are not suitable for industrial production. , harsh reaction conditions, etc.

Active Publication Date: 2017-11-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The technical problem to be solved by the present invention is to overcome the existing problems in the existing method for synthesizing alkyl trifluoromethyl sulfides, the substrate needs to be pre-functionalized, the reaction conditions are harsh, the trifluoromethyl thio reagent is not easy to obtain, and the cost High, difficult and unsuitable for technical problems such as industrial production, and provide an alkyl trifluoromethyl sulfide compound and its preparation method

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
  • A kind of alkyl trifluoromethyl sulfide compound and preparation method thereof
  • A kind of alkyl trifluoromethyl sulfide compound and preparation method thereof
  • A kind of alkyl trifluoromethyl sulfide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0048] Example 1 C-H direct trifluoromethylthiolation reaction of cyclooctane, silver trifluoromethylthio and potassium persulfate

[0049]

[0050] Add silver trifluoromethylsulfanyl (0.5mmol), N-hydroxyphthalimide (0.1mmol) and potassium persulfate (1.0mmol) into the reaction flask, add cyclooctane (1.0mmol) after pumping argon three times mmol) and acetonitrile (5 mL). The reaction bottle was placed in an oil bath at 80°C and started to heat and stir for 4 hours, then took it out, and cooled to room temperature. With benzotrifluoride as the internal standard substance, using 19 F-NMR confirmed the formation of cyclooctyl trifluoromethyl sulfide (yield 82%). The reaction solution was filtered, and the filtrate was used to remove the solvent by a rotary evaporator, and separated by bottle-neck-bottle distillation to obtain a colorless oily liquid (64 mg, yield 60%). The relevant data are as follows: 1 H NMR (400MHz, CDCl 3 ): δ3.51-3.44(m,1H),2.09-2.02(m,2H),1.80-1.71...

Embodiment 2

[0051] Example 2 The decarboxylation trifluoromethylthiolation of cyclohexanecarboxylic acid, silver trifluoromethylthio and potassium persulfate

[0052]

[0053]Silver trifluoromethylthio (1.5mmol), pyridine (0.1mmol) and potassium persulfate (4.5mmol) were added to the reaction flask, and cyclohexanecarboxylic acid (1.0mmol) and acetonitrile (20mL) were added after argon was pumped three times. Place the sealed tube in an oil bath at 60°C and start heating and stirring for 24 hours, then take it out, and let it cool to room temperature. With benzotrifluoride as the internal standard substance, using 19 F-NMR confirmed the formation of cyclohexyltrifluoromethylsulfide (83% yield). Formation of this product was also confirmed by GC-MS. The relevant data are as follows: m / z=184 (GC-MS; EI).HRMS-EI: Calculated for C 7 h 11 f 3 S:184.0534,Found:184.0535.Crude 1 H NMR (400MHz, CD 3 CN): δ3.35(tt,J=4Hz,1H),2.06-1.27(m,10H)ppm.Crude 19 F NMR (376MHz, CD 3 CN):δ-39.78(s,...

Embodiment 3

[0054] Coupling reaction of embodiment 3 cyclodecyl boronic acid, silver trifluoromethylthio and potassium persulfate

[0055]

[0056] Add silver trifluoromethylthio (0.5mmol), o-phenanthroline (0.5mmol) and potassium persulfate (1.0mmol) into the reaction flask, add cyclodecylboronic acid (3.0mmol) and Acetonitrile (15 mL). Place the sealed tube in an oil bath at 25°C and start heating and stirring for 36 hours, then take it out, and wait to cool to room temperature. With benzotrifluoride as the internal standard substance, using 19 It was confirmed by F-NMR that cyclodecyltrifluoromethylsulfide was produced (yield: 74%). The reaction solution was filtered, and the filtrate was used to remove the solvent by a rotary evaporator, and separated by bottle-neck-bottle distillation to obtain a colorless oily liquid (65 mg, yield 55%). The relevant data are as follows: 1 H NMR (400MHz, CDCl 3 ):δ3.58-3.51(m, characteristic CH-SCF 3 ),1.97-1.79(m,4H),1.65-1.63(m,4H).1.54-1....

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 an alkyl trifluoromethyl sulfide compound and a preparation method thereof. The method comprises the following steps: under the protection of an inert gas, the alkyl substrate and a trifluoromethylthio reagent are subjected to a trifluoromethylthiolation reaction; the trifluoromethylthio reagent includes the following components: Fluoromethylthio metal salts, oxidizing agents and nitrile solvents. The trifluoromethylthio reagent of the present invention is cheap and easy to obtain, and when used to synthesize alkyl trifluoromethyl sulfide compounds, it can quickly and conveniently introduce trifluoromethylthio to an alkyl substrate without pre-functionalization, and the synthesis The method has a wide range of substrates, mild reaction conditions, high reaction efficiency, the most direct reaction, simple operation, low cost, and is more suitable for industrial production.

Description

technical field [0001] The invention relates to an alkyl trifluoromethyl sulfide compound and a preparation method thereof. Background technique [0002] Fluorine atom is the ninth element in the periodic table and belongs to group VIIA. Its atomic radius is close to that of hydrogen atom and has the strongest electronegativity. The C-F bond has a high bond energy, and the bond length is the closest to the C-H bond length. . It is precisely because of these characteristics of fluorine atoms that fluorine-containing organic compounds exhibit a series of unique physical and chemical properties, which have very important application values ​​in the fields of medicine, pesticides, and materials. Currently, 20% to 30% of pharmaceuticals and 30% to 40% of agricultural chemicals contain at least one fluorine atom. Among various fluorine-containing functional groups, trifluoromethylthio (-SCF 3 ) plays an important role due to its strong electronegativity and strong lipophilicity...

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 Patents(China)
IPC IPC(8): C07B45/06C07C319/14C07C323/03C07C323/22C07C323/12C07C323/13C07D209/48
Inventor 陈庆云刘超吴浩肖智伟
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