Prepn process of 4-amino-2-trifluoromethyl benzonitrile

A technology of trifluoromethyl benzonitrile and trifluoromethyl fluorobenzene, applied in the field of preparing 4-amino-2-trifluoromethyl benzonitrile, can solve the problem of high production cost, many raw materials, many by-products, etc. problems, to achieve the effect of low production cost, simple process and easy access to raw materials

Inactive Publication Date: 2006-08-02
唐保清 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] It can be clearly seen from the above technical route that many raw materials are used in the diazotization step, such as hydrobromic acid, sodium hydroxide, sodium nitrite and other raw materials are required, the operation is cumbersome, there are many by-products, which must be purified, and the adjacent trifluoro The yield of methyl bromide is low, only about 60%
In the iron powder reduction step, the target must be extracted with a solvent. During the extraction process, 4-amino-2-trifluoromethylbenzonitrile is easy to mix with the iron powder, so

Method used

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  • Prepn process of 4-amino-2-trifluoromethyl benzonitrile

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Effect test

Embodiment 1

[0017] The first step of positioning bromination: put 200kg m-trifluoromethylfluorobenzene, 80kg glacial acetic acid, and 35kg concentrated sulfuric acid into the reaction pot, mix and stir, heat up and reflux, add 188kg dibromohydantoin in batches, react for 6 hours, and store on ice Wash with water to obtain 260kg of 4-fluoro-2-trifluoromethyl bromide, with a content of more than 98%;

[0018] The second step of cyano group replacement: Take 250kg quinoline and 106kg cuprous cyanide and add dropwise the 4-fluoro-2-trifluoromethylbromobenzene obtained in the first step under the state of stirring and reflux. Distill 200kg of 4-fluoro-2-trifluoromethylbenzonitrile;

[0019] The third step of ammonolysis and substitution: dissolve the 4-fluoro-2-trifluoromethylbenzonitrile obtained in the second step in 350 kg of ethanol, feed in 27 kg of liquid ammonia, and heat up to 120°C for 8 hours to obtain 4- Amino-2-trifluoromethylbenzonitrile crude product 185kg, finally obtains finis...

Embodiment 2

[0022] The first step of positioning bromination: put 250kg of m-trifluoromethylfluorobenzene, 100kg of glacial acetic acid, and 44kg of concentrated sulfuric acid into the reaction pot, mix and stir, heat up and reflux, add 235kg of dibromohydantoin in batches, react for 6.5 hours, and store on ice Wash with decomposed water to obtain 4-fluoro-2-trifluoromethyl bromobenzene;

[0023] The second step of cyano replacement: take 310kg of quinoline and 132kg of cuprous cyanide and add dropwise the 4-fluoro-2-trifluoromethylbromobenzene obtained in the first step under the state of stirring and reflux. 4-fluoro-2-trifluoromethylbenzonitrile is distilled off;

[0024] The third step of ammonolysis and substitution: dissolve the 4-fluoro-2-trifluoromethylbenzonitrile obtained in the second step in 440 kg of ethanol, pass through 34 kg of liquid ammonia, and heat up to 122 ° C for 10 hours to obtain 4- Amino-2-trifluoromethylbenzonitrile crude product 211kg, finally obtains finished...

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Abstract

The present invention discloses improved process of preparing 4-amino-2-trifluoromethyl benzoitrile. The present invention prepares 4-amino-2-trifluoromethyl benzoitrile with trifluoro methyl fluorobenzene as main material and through three steps of positioning bromination, cyano group replacement and aminolysis substitution. The preparation process uses marketable glacial acetic acid, concentrated sulfuric acid, dibromo hydantoin, cuprous cyanide, liquid ammonia and alcohol, and has less consumption of strong acid and cuprous cyanide. The preparation process has facile materials, simple operation, short path, product purity over 99 % and total product yield up to 73-75 %, less exhaust of harmful matter, and low production cost.

Description

Technical field: [0001] The invention relates to a method for preparing 4-amino-2-trifluoromethylbenzonitrile. technical background: [0002] Bicalutamide is an anti-androgen non-corticosteroid, widely used in the treatment and prevention of prostate cancer, pancreatic cancer, breast cancer and other chronic diseases. Bicalutamide is well tolerated, without any steroidal effect after taking it, and has no obvious side effects on blood vessels and metabolism. Few patients (including the elderly) stop taking the drug because of adverse reactions. The drug was developed and produced by Casodex (Zeneca, UK). It was launched in the UK in 1994, and was subsequently approved for marketing in dozens of countries and regions including the US and China. According to the verification from the State Medical Administration, the administrative protection period of bicalutamide (imported) in my country has expired in October 2005. All domestic pharmaceutical manufacturers can produce bic...

Claims

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Application Information

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IPC IPC(8): C07C255/58C07C253/14
Inventor 唐保清
Owner 唐保清
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