Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide

A technology of phenylbistrifluoromethanesulfonimide and phenyltrifluoromethanesulfonamide, which is applied in the field of preparation of N-phenylbistrifluoromethanesulfonimide, and can solve the problem that the reaction product has many impurities and high cost , high price of trifluoromethanesulfonic acid, etc.

Inactive Publication Date: 2020-06-12
江苏笃行致远新材料科技有限公司
View PDF10 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are following key problems in this method: 1) the raw material trifluoromethanesulfonic anhydride is expensive, and at least 2eq will be used, so the production cost is high; 2) the exothermic stage of the reaction system is severe in the early stage, and trifluoromethanesulfonic anhydride needs to be added dropwise at low temperature ; 3) The reaction product has many impurities and low product purity, resulting in low product purity, and the highest yield can reach 86%; and if the yield wants to reach more than 90%, three conditions must be met simultaneously: inert gas protection, low temperature control, slow Slow drop (JP JP2003286244)
The key problem of this method is: 1) raw material trifluoromethanesulfonic acid price is

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
  • Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide
  • Preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 9.3 kg of aniline, 40 L of acetonitrile, and 13 kg of triethylenediamine into a 100L stainless steel reactor, and connect the trifluoromethanesulfonyl fluoride steel cylinder; evacuate the reactor to -0.09Mpa, and feed 20 kg of trifluoromethanesulfonyl fluoride Gas, seal the reactor; stir and react at 40°C for 8 hours, observe that the pressure of the reactor gradually decreases from 0.23Mpa to 0.08Mpa, and maintains no significant change within half an hour.

[0049] Open the acyl fluoride recovery pipeline, reclaim excessive acyl fluoride, after the reactor pressure is reduced to 0Mpa, close the acyl fluoride recovery pipeline. Open the distillation system, and distill off 34L of acetonitrile. Add 40L dichloromethane in reactor again, 0.4 kilogram of 4-dimethylaminopyridine, pass into 20 kilograms of trifluoromethanesulfonyl fluoride again, closed reaction 15 hours, reactor pressure is reduced to 0.06Mpa by 0.21Mpa.

[0050] Recover excess trifluoromethanesulfony...

Embodiment 2

[0052] Add 9.3 kg of aniline, 35 L of dimethylformamide, and 33 kg of DBU into a 100 L stainless steel reactor, and connect the trifluoromethanesulfonyl fluoride steel cylinder. Reactor is evacuated to-0.09Mpa, feeds 22 kilograms of trifluoromethanesulfonyl fluoride gas, and seals reactor. Stirring and reacting at 60°C for 8 hours, the pressure of the reactor gradually decreased from 0.29Mpa to 0.09Mpa, and there was no obvious change within half an hour. Open the acyl fluoride recovery pipeline, reclaim excessive acyl fluoride, after the reactor pressure is reduced to 0Mpa, close the acyl fluoride recovery pipeline. Open distillation system, distill and remove 30L dimethylformamide. Then add 50L of toluene, 0.3 kg of 4-dimethylaminopyridine, pass into 25 kg of trifluoromethanesulfonyl fluoride again, close the reaction at 60 ° C for 10 hours, the pressure of the reactor is reduced from 0.26Mpa to 0.1Mpa, and recover the excess trifluoromethane Sulfonyl fluoride, 38L of solv...

Embodiment 3

[0054] Add 9.3 kg of aniline, 45 L of acetonitrile, and 15 kg of triethylenediamine into a 100 L stainless steel reactor, and connect the trifluoromethanesulfonyl fluoride steel cylinder. Reactor is evacuated to-0.09Mpa, feeds 30 kilograms of trifluoromethanesulfonyl fluoride gas, and seals reactor. Stirring and reacting at room temperature for 8 hours, the pressure of the reactor gradually decreased from 0.25Mpa to 0.1Mpa, and there was no obvious change within half an hour. Open the acyl fluoride recovery pipeline, reclaim excessive acyl fluoride, after the reactor pressure is reduced to 0Mpa, close the acyl fluoride recovery pipeline. Open distillation system, remove 40L acetonitrile by distillation. Then add 45L dichloromethane, 0.4 kilograms of 4-dimethylaminopyridine, pass into 23 kilograms of trifluoromethanesulfonyl fluoride again, seal reaction 16 hours, reactor pressure is reduced to 0.06Mpa by 0.22Mpa, reclaim excessive trifluoromethane Sulfonyl fluoride, 40L of so...

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 a preparation method of N-phenyl bis (trifluoromethanesulfonyl) imide. According to the method, trifluoromethanesulfonyl fluoride is adopted as a raw material, in a strong polar solvent, organic alkali is adopted as an acid-binding agent to react with aniline to generate N-phenyl trifluoromethanesulfonamide, most of the solvent is removed through distillation, a weak polarsolvent and a catalyst are added, trifluoromethanesulfonyl fluoride continues to be introduced for the reaction, and N-phenyl bis (trifluoromethanesulfonyl) imide is prepared. According to the scheme,the cost is low, the reaction is mild, excessive trifluoromethanesulfonyl fluoride cannot be discharged to generate pollution without using shielding gas, the prepared product is high in purity and yield, and industrial popularization can be achieved.

Description

technical field [0001] The invention belongs to the field of fine chemicals, in particular to a preparation method of N-phenyl bistrifluoromethanesulfonimide. Background technique [0002] N-Phenylbistrifluoromethanesulfonyl imide is a highly efficient trifluoromethanesulfonylating reagent that can be used for the trifluoromethylsulfonylation of enols, phenols, and amines without reacting with alcohols. Therefore, it is widely used in the synthesis of pharmaceutical intermediates and material intermediates. And used in the synthesis of anti-prostate cancer drug Abiraterone. [0003] The synthetic route of N-phenyl bis-trifluoromethanesulfonimide has so far the following three: [0004] Scheme 1: [0005] [0006] Scheme 2: [0007] [0008] For Scheme1, many patents and literatures have been reported. 如专利CN106518759、CN103717214CN102250065、CN105979779、JP2003286244、US20110230495、 WO2015112441、WO2016027284,文献Tetrahedron Letters,46,4607-10,1973和Inorganic Chemistry,49(3...

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): C07C303/38C07C303/36C07C311/08C07C311/48
CPCC07C303/36C07C303/38C07C311/08C07C311/48
Inventor 刘智慧崔志鹏郭敬维韩贵芳李欣
Owner 江苏笃行致远新材料科技有限公司
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