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

A method for synthesizing 2-bromo-n-p-methylbenzenesulfonylpyrrole

A technology of toluenesulfonylpyrrole and toluenesulfonyl chloride, which is applied in the field of synthesizing 2-bromo-N-p-methylbenzenesulfonylpyrrole, can solve the problem of 2-bromopyrrole with a purity of only 85% and cannot be separated and purified. Instability and other problems, to achieve the effect of easy reaction, easy industrial production, and good purity

Inactive Publication Date: 2015-12-02
成都安斯利生物医药有限公司
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are some problems with this synthetic route, the first being the use of Br 2 -Me-hydantion carries out the ortho-position bromination of pyrrole. In this step, bromine substitution reactions at different positions of pyrrole will occur, and a multi-position bromine-substituted pyrrole mixture is generated. Moreover, 2-bromopyrrole is extremely unstable at room temperature and cannot Separation and purification, directly adding p-toluenesulfonic acid chloride for the next step reaction, and then post-processing, purification, the yield of the obtained target product is only 20%, and the purity is only 85%

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 method for synthesizing 2-bromo-n-p-methylbenzenesulfonylpyrrole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] One, the preparation of N-p-toluenesulfonate pyrrole:

[0022] Add 100g, 1.491mol of pyrrole and 165.96g, 1.64mol of triethylamine into a 3L reaction flask, then add 1500mL of anhydrous ether, cool to 0°C, slowly add 284.10g, 1.491mol of p-toluenesulfonyl chloride dropwise, and react The system was warmed up to room temperature, reacted at room temperature for 6 h, added saturated NH4Cl solution, separated the organic phase, washed with water, washed with saturated brine, dried with anhydrous magnesium sulfate, and distilled off the solvent to obtain a white solid compound;

[0023] Two, the synthesis of 2-bromo-N-p-toluenesulfonate pyrrole:

[0024] Under the protection of nitrogen, add 100g, 0.45mol N-p-toluenesulfonate pyrrole and 1000mL tetrahydrofuran to a 3L reaction flask, cool to -78°C, slowly add 292mL, 0.50mol, 1.7Ninhexanes tert-butyl lithium dropwise, and complete the addition , reacted at 78°C for 3h, then added dropwise 47.88g, 0.45molBrCN in 100mL tetrah...

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 method for synthetising 2-bromine-N-methyl benzenesulfonyl pyrrole, relates to organic synthetic chemistry, and belongs to the field of medicines and chemical engineering. The method is characterized by comprising the following steps: firstly, a benzenesulfonyl reaction is conducted on pyrrole nitrogen to generate a stable intermediate compound; then, tert-butyllithium is allowed to highly selectively be subjected to lithiation reaction with ortho-position hydrogen of N-methyl benzenesulfonyl pyrrole; finally, the product is allowed to react with BrCN to obtain the target compound. The method has the benefits that the yield of the target compound is high, the total yield of the two steps of reactions reaches more than 50%, the purity is high, the reactions are easy to operate, the performance is high, and the industrial production is easy to realize.

Description

technical field [0001] The invention relates to organic synthesis chemistry, belongs to the technical fields of medicine and chemical industry, and specifically relates to a method for synthesizing 2-bromo-N-p-toluenesulfonylpyrrole. Background technique [0002] 2-Bromo-N-p-toluenesulfonate pyrrole is widely used in chemical reagents, fine chemicals, pharmaceutical intermediates, and material intermediates. Other functionalization reactions can be carried out through the bromine at the 2-position to generate pyrrole derivatives, and the protecting group p-toluenesulfonic acid group can also be removed to generate free pyrrole. For the synthesis of this compound, there are some literature reports, and its synthetic route is as follows: [0003] [0004] There are some problems with this synthetic route, the first being the use of Br 2 -Me-hydantion carries out the ortho-position bromination of pyrrole. In this step, bromine substitution reactions at different positions ...

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): C07D207/48
CPCC07D207/48
Inventor 唐拥军莫珊
Owner 成都安斯利生物医药有限公司
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