Synthesis method of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride and application of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride in antitumor drugs

A technology of trifluoromethylbenzamide group and trifluoromethylaniline, which is applied in the synthesis field of triphenyl-4-butylphosphonium chloride, can solve the problems of difficult control, low product purity of quaternary phosphonium salt, and poor product purity. It can reduce the excessive proportion of side reactions, overcome the harsh synthesis conditions, and reduce the reaction temperature.

Inactive Publication Date: 2018-12-28
HUBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2007, Xiao Chunfen, Zhou Li, Kui Lanhua, and Lou Zhaowen published a basic research achievement "Synthesis and Characterization of Several Triphenyl-substituted Alkyl Quaternary Phosphonium Salts", using phenol as raw material and chloroalkanoyl chloride as linking group Synthesized 4 phenoxycarbonyl alkyl triphenyl quaternary phosphonium salts, but due to the cytotoxicity of the raw material phenol and the low purity of the obtained quaternary phosphonium salts, it is not suitable for use in antitumor

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  • Synthesis method of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride and application of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride in antitumor drugs
  • Synthesis method of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride and application of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride in antitumor drugs
  • Synthesis method of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride and application of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride in antitumor drugs

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Embodiment 1

[0036] A kind of synthetic method of triphenyl-4-(m-trifluoromethylbenzamido) butylphosphonium chloride of the present embodiment comprises the following steps:

[0037] (1) Synthesis of N-trifluoromethylphenyl-4-chlorobutanamide

[0038] Dissolve 0.82g (5mmol) m-trifluoromethylaniline in 15ml chloroform in the reaction flask, then add 0.50g (5mmol) triethylamine, control the temperature in an ice-water bath, stir, then slowly add 4 -Chlorobutyryl chloride 0.84g (6mmol), after reacting for 20min, remove the ice bath, continue to heat and reflux, react for 2.5h, TLC monitors the reaction process, until the reaction is complete, use saturated Na 2 CO 3 After the solution was washed, it was washed with saturated brine, and then extracted twice with 15ml chloroform, the organic phases were combined and then washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, separated by column chromatography, and separated wit...

Embodiment 2

[0042] A kind of synthetic method of triphenyl-4-(m-trifluoromethylbenzamido) butylphosphonium chloride of the present embodiment comprises the following steps:

[0043] (1) Synthesis of N-trifluoromethylphenyl-4-chlorobutanamide

[0044] Dissolve 0.82g (5mmol) m-trifluoromethylaniline in 15ml chloroform in the reaction flask, then add 0.53g (5mmol) sodium carbonate solid, control the temperature in an ice-water bath, stir, then slowly add 4 -Chlorobutyryl chloride 0.84g (6mmol), after reacting for 30min, remove the ice bath, continue to heat and reflux, react for 5h, TLC monitors the reaction progress, until the reaction is complete, use saturated Na 2 CO 3 solution, then washed with saturated brine, extracted twice with 15ml chloroform respectively, the organic phases were combined and then washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, separated by column chromatography, and separated with solvent...

Embodiment 3

[0048] A kind of synthetic method of triphenyl-4-(o-trifluoromethylbenzamido) butylphosphonium chloride of the present embodiment comprises the following steps:

[0049] (1) Synthesis of N-o-trifluoromethylphenyl-4-chlorobutanamide

[0050] Dissolve 0.33 g (2 mmol) of o-trifluoromethylaniline in 10 ml of chloroform in a reaction flask, add 0.20 g (2 mmol) of triethylamine, control the temperature in an ice-water bath, stir, and slowly add 4- Chlorobutyryl chloride 0.36 g (2.6 mmol). After reacting for 20min, remove the ice bath, continue to heat and reflux, react for 2.5h, TLC monitors the reaction process, until the reaction is complete, use saturated Na 2 CO 3 solution, then washed with saturated brine, extracted twice with 15ml chloroform respectively, the organic phases were combined and then washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, separated by column chromatography, and diethyl ether and...

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Abstract

The invention relates to a synthesis method of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride and an application of triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride inantitumor drugs, and belongs to the technical field of organic synthesis. The method comprises the following steps: taking o-trifluoromethylaniline, m-trifluoromethylaniline and p-trifluoromethylaniline as raw materials, chloroform as a solvent and sodium carbonate, triethylamine, pyridine and the like as an acid binding agent to be subjected to reaction with 4-chlorobutyryl chloride so as to obtain a first-grade product, and performing reflux on the obtained first-grade product and triphenylphosphine in the solvent to obtain the final product trifluoromethylbenzamide triphenyl quaternary phosphonium salt. The target product is not limited by the types of the acid binding agents and solvents, and defects of harsh synthesis conditions, uneasy control and low purity of the synthesized product in the prior art are overcome; besides, the step-by-step elution procedure is introduced into purification of the final product, the selected specific eluent ensures purity of the final product. Theraw materials are widely sourced, cheap and easily available, and the prepared quaternary phosphonium salt compound is low in toxicity and efficient, and triphenyl-4-(trifluoromethylbenzamide)butylphosphonium chloride can be applied to preparation of the antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis and application of a fluorine-containing phosphorus nitrogen compound (FPN). More specifically, the invention relates to a chlorinated triphenyl-4-(trifluoromethylbenzamide ) Synthetic method of butylphosphonium and its application in antineoplastic drugs. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. More than 7 million people die from malignant tumors every year in the world. Cancer is becoming the number one killer of human beings. Due to the characteristics of tumor cell proliferation and metastasis, radiotherapy, chemotherapy, and surgical treatment cannot achieve the goal of radical cure, and chemotherapy techniques generally have problems such as individual differences, side effects, and drug dependence, and the therapeutic effect has always reached Therefore, it is...

Claims

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Application Information

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IPC IPC(8): C07F9/54A61P35/00
CPCC07F9/5442A61P35/00
Inventor 娄兆文张杰肖春芬陈兰肖成林周莉
Owner HUBEI UNIV
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