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

Synthesis method of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyl epoxypropylene-2-amide

A technology of methyl epoxy propylene and trifluoromethyl phenyl is applied in the field of synthesis of N-phenyl)-2-methyl epoxy propylene-2-amide, which can solve the instability of peroxide and processing cost problems such as rising and environmental unfriendliness, and achieve the effect of high safety in production operation, low environmental pollution, and simple and easy post-processing

Active Publication Date: 2020-05-01
SUZHOU UUGENE BIOPHARMA
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] 1. Methacryloyl chloride is used in the condensation process, which is highly toxic and releases a large amount of waste acid gas during the reaction, which is very unfriendly to the environment
[0010] 2. The whole system is strongly acidic, requiring equipment with excellent acid resistance, and the absorption and treatment of waste acid gas will lead to an increase in processing costs
[0011] 3. Hydrogen peroxide is used as peroxide in the oxidation process. The instability of peroxide leads to a great risk in the production process, but the yield of this method is only 88%.

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
  • Synthesis method of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyl epoxypropylene-2-amide
  • Synthesis method of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyl epoxypropylene-2-amide
  • Synthesis method of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyl epoxypropylene-2-amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: In a 500L reactor, 18.6kg of 4-amino-2-trifluoromethylbenzonitrile and 19.9kg of methyl methacrylate and 200kg of dichloromethane and 100g of DMF were heated up by 30 degrees , reacted for 3h, pulled dichloromethane dry, and added 200kg of water into a 500L reactor, cooled to 20 degrees and filtered to obtain 23kg of light yellow solid, which was intermediate N-(4-cyano-3- Trifluoromethylphenyl)methacrylamide;

[0042] Add the above-mentioned 23kg of intermediates, 230kg of water, 2.3kg of tetrabutylammonium bromide and 0.23kg of manganese dioxide into a 500L reactor, stir for 0.5h and raise the temperature to 47 degrees, keep 47 degrees, pass into Air, kept at 45-50 degrees for 12 hours, cooled to 20-25 degrees, filtered, dried to obtain 24kg of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene -2-amide, yield 98%, purity 99.42%.

Embodiment 2

[0043] Example 2: In a 500L reactor, 18.6kg of 4-amino-2-trifluoromethylbenzonitrile and 19.9kg of methyl methacrylate and 200kg of toluene and 100g of DMF were heated up by 30 degrees to react 3h, pull the toluene dry, and add 200kg of water into a 500L reaction kettle, cool down to 20 degrees and filter to obtain 17kg of light yellow solid, which is the intermediate N-(4-cyano-3-trifluoromethyl Phenyl)methacrylamide;

[0044] Add the above-mentioned 17kg of intermediates, 170kg of water, 1.7kg of tetrabutylammonium bromide and 0.17kg of manganese dioxide into a 500L reactor, stir for 0.5h and raise the temperature to 47 degrees, keep 47 degrees, pass into Air, kept at 45-50 degrees for 12 hours, cooled to 20-25 degrees, filtered, dried to obtain 17kg of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene -2-amide, yield 69.4%, purity 87.62%.

Embodiment 3

[0045]Example 3: In a 500L reactor, 18.6kg of 4-amino-2-trifluoromethylbenzonitrile and 19.9kg of methyl methacrylate and 200kg of dichloromethane and 100g of DMF were heated up by 30 degrees , reacted for 3h, pulled dichloromethane dry, and added 200kg of water into a 500L reactor, cooled to 20 degrees and filtered to obtain 23kg of light yellow solid, which was intermediate N-(4-cyano-3- Trifluoromethylphenyl)methacrylamide;

[0046] Add the above-mentioned 23kg of intermediates, 230kg of water, 1.5kg of tetrabutylammonium bromide and 0.15kg of manganese dioxide into a 500L reactor, stir for 0.5h and raise the temperature to 47 degrees, keep 47 degrees, pass into Air, kept at 45-50 degrees for 12 hours, cooled to 20-25 degrees, filtered, dried to obtain 11kg of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene -2-amide, yield 44.4%, purity 91.42%.

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

PropertyMeasurementUnit
wavelengthaaaaaaaaaa
Login to View More

Abstract

The invention discloses a synthesis method of N-(4-cyano-3-(trifluoromethyl) phenyl)-2-methyl epoxypropylene-2-amide, which comprises the following processing steps: S1, dissolving 4-amino-2-trifluoromethyl benzonitrile and a catalyst in dichloromethane, adding methyl methacrylate, heating the liquid to 10-65 DEG C, and reacting for 1-10 hours; S2, after the reaction is finished, cooling and filtering the reaction product and drying the reaction product to remove dichloromethane to obtain N-(4-cyano-3-trifluoromethylphenyl)methacrylamide; S3, adding the N-(4-cyano-3-trifluoromethylphenyl)methacrylamide into a solvent, adding a biphasic catalyst and manganese dioxide, and stirring the mixture for 1 to 3 hours; S4, performing a reaction on the mixture liquid for 10-24 hours, cooling a reaction product to 20-25 DEG C, and filtering and drying the reaction product to obtain the N-(4-cyano-3-(trifluoromethyl)phenyl)-2-methyl epoxypropylene-2-amide. The biphasic catalyst is cyclic crown ethers. Raw materials used in the method are easy to obtain and low in price, reagents and solvents used in the method are of conventional industrial specifications, and the method is suitable for industrial production, extremely small in environmental pollution, low in equipment requirement and high in operation safety.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide. Background technique [0002] N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide, the chemical formula is: [0003] [0004] N-(4cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide is a key intermediate of bicalutamide for the treatment of advanced prostate cancer. [0005] Patents related to the synthesis of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide in the prior art (Patent No. US2004 / 68135,2004, A1) The method specifically disclosed in this patent is: [0006] [0007] The method starts from 4-amino-2-trifluoromethylbenzonitrile, reacts with methacryloyl chloride to obtain N-(4-cyano-3-trifluoromethylphenyl)methacrylamide, and then passes Oxidation of hydrogen peroxide is a process for preparing important pha...

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): C07D303/46C07D301/08
CPCC07D303/46C07D301/08
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE BIOPHARMA
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