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The synthetic method of n-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide

A technology of methyl epoxy propylene and trifluoromethyl, which is applied in the field of synthesis of N-phenyl)-2-methyl epoxy propylene-2-amide, can solve peroxide instability, rising processing costs, Unfriendly to the environment and other issues, to achieve the effect of high safety in production operation, low environmental pollution, and simple and easy post-processing

Active Publication Date: 2022-05-10
SUZHOU UUGENE BIOPHARMA
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  • 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

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  • The synthetic method of n-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide
  • The synthetic method of n-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-2-amide
  • The synthetic method of n-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropene-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 the dichloromethane dry, and added 200kg of water into a 500L reaction kettle, cooled to 20 degrees and filtered to obtain 23kg of light yellow solid, which was the 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%.

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Abstract

The invention discloses a synthesis method of N-(4 cyano-3-(trifluoromethyl)phenyl)-2-methylepoxypropylene-2-amide, which comprises the following processing steps: S1, combining 4- Dissolve amino-2-trifluoromethylbenzonitrile and catalyst in dichloromethane, add methyl methacrylate, raise the temperature to 10~65°C, and react for 1~10h; S2, after the reaction, cool down and filter to dichloro Methane is dried to obtain N-(4-cyano-3-trifluoromethylphenyl) methacrylamide; S3, N-(4-cyano-3-trifluoromethylphenyl) methacrylamide Add to the solvent, add biphasic catalyst and manganese dioxide, stir for 1~3h; S4, pass through the reaction in the mixed solution for 10~24h, cool down to 20~25°C, filter and dry to obtain N‑(4cyano‑ 3‑(trifluoromethyl)phenyl)‑2‑methylepoxypropylene‑2‑amide; the biphasic catalyst is a cyclic crown ether. The raw materials used in the invention are readily available and cheap, and the reagents and solvents used are conventional industrial specifications, suitable for industrial production, with minimal environmental pollution, low equipment requirements and high operational 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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/46C07D301/08
CPCC07D303/46C07D301/08
Inventor 高元崔槐杰宗杨磊
Owner SUZHOU UUGENE BIOPHARMA
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