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Preparation method of nilutamide

A cyanochlorobenzene and recrystallization technology, applied in the direction of organic chemistry, etc., can solve the problems of large amount of post-treatment wastewater, difficulty in purchasing propane, and high reaction temperature, and achieve the effects of low cost, less solvent in the system, and simple synthesis route

Inactive Publication Date: 2018-06-29
WUJIANG XINKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the route one reaction, it is necessary to use the highly toxic substance solid phosgene to prepare 3-trifluoromethyl-4-cyanophenyl isocyanate; the raw material 2-amino-2-cyanopropane is not easy to purchase, and the highly toxic substance cyanide is required for preparation ; During the hydrolysis process, hydrochloric acid heating is required, which will cause great corrosion to the equipment
[0005] The diazotization in the route two reaction will produce a large amount of acidic wastewater, which is not conducive to environmental protection
The second step is reflux reaction in 10 times the volume of N,N-dimethylformamide, the reaction temperature is high, and the amount of post-treatment wastewater is large

Method used

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  • Preparation method of nilutamide

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Effect test

Embodiment 1

[0019] Add 100mL dimethyl sulfoxide to a 250ml three-necked bottle, add 30g of 5,5-dimethylhydantoin at one time, then add 50g of 3-trifluoromethyl-4-cyanochlorobenzene, and then add 0.5g of Potassium iodide and 20 g of potassium hydroxide were heated to 80° C. for 6 hours. After the reaction was complete, cooled to room temperature, the reaction solution was poured into water, and 58 g of a yellow solid was obtained by filtration. The crude product was recrystallized from ethanol to obtain 48 g of pure nilutamide, with a yield of 66.3%.

Embodiment 2

[0021] Add 10L dimethyl sulfoxide to a 30L reactor, add 3Kg 5,5-dimethylhydantoin at one time, then add 5Kg3-trifluoromethyl-4-cyanochlorobenzene, and then add 50g of potassium iodide, 2Kg Potassium hydroxide, then heated to 80 ° C for 6 hours, after the reaction was complete, cooled to room temperature, the reaction solution was poured into water, and filtered to obtain 5.5 Kg of a yellow solid. The crude product was recrystallized from toluene to obtain 4.7 kg of pure nilutamide with a yield of 65%.

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Abstract

The invention discloses a preparation method of nilutamide; 3-trifluoromethyl-4-cyanochlorobenzene as a raw material and 5,5-dimethyl hydantoin undergo a reaction in a dimethyl sulfoxide solvent underthe alkalinity and the catalysis of potassium iodide, and an obtained crude product is purified by recrystallization. The method provided by the invention has the advantages of short reaction steps,mild reaction conditions and less environmental pollution.

Description

technical field [0001] The invention relates to a preparation method of nilutamide, which belongs to the technical field of chemical synthesis. Background technique [0002] The chemical formula of Nilutamide is a non-steroidal anti-androgen drug similar to flutamide, which can bind to androgen receptors without androgen effect, thereby blocking the combination of androgen and these receptors, and acting as an anti-androgen effect. For the treatment of prostate cancer or metastatic prostate cancer, it can be combined with surgery and chemotherapy. [0003] Nimirut is usually prepared by the following two methods: Route 1: 3-trifluoromethyl-4-cyanophenyl isocyanate is obtained by reacting 3-trifluoromethyl-4-cyanoaniline with phosgene, and then It can be cyclized with 2-amino-2-cyanopropane and hydrolyzed to obtain nimirut. Route 2: Prepare 3-trifluoromethyl-4-cyanoiodobenzene from 3-trifluoromethyl-4-cyanoaniline by diazotization, and then react with 5,5-dimethylhydantoin...

Claims

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Application Information

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IPC IPC(8): C07D233/72
CPCC07D233/72
Inventor 魏海洋胡立文皱培欢严雅婷
Owner WUJIANG XINKAI MEDICAL TECH
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