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Synthetic method and application of urea compound

A synthesis method and compound technology, which is applied in the field of synthesis of urea compounds, can solve the problems of using unstable starting materials and being expensive, and achieve the effects of low cost, easy raw materials, and mild reaction conditions

Inactive Publication Date: 2019-05-21
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the scope of these transition metal-catalyzed conversions is usually limited by the use of unstable starting materials, expensive catalysts and ligands, multiple additives, harsh conditions involving high pressure and temperature, requiring careful handling and creating environmentally unfriendly waste.
Therefore, an environmentally friendly and facile method for the synthesis of asymmetric N,N′-substituted diarylureas has been a challenging research

Method used

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  • Synthetic method and application of urea compound
  • Synthetic method and application of urea compound
  • Synthetic method and application of urea compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 A method for preparing urea compounds, preparing the compound represented by formula I-a

[0019]

[0020] The preparation steps are as follows: In the air, add magneton, 3-phenyl-1,4,2-oxazol-5-one (0.3mmol), sodium acetate (0.3mmol) and a 10mL round bottom flask. Methanol (1 mL), add aniline (0.3 mmol) under stirring. Then plug the rubber stopper and heat and stir in an oil bath at 60°C for 2h. After the reaction is completed, petroleum ether / ethyl acetate is selected as the mobile phase, and the product is purified by flash silica gel column chromatography.

[0021] The yield was 99%. The structure of the compound represented by formula I-a is characterized as follows: white solid, 1 H NMR (500MHz, DMSO): δ8.66 (2H, s), 7.46 (4H, dd, J = 8.5, 1.0 Hz), 7.28 (4H, td, J = 7.5, 1.5 Hz), 6.96 (4H, tt ,J=7.5,1.0Hz); 13 C NMR(125MHz,DMSO):δ152.5,139.7,128.8,121.8,118.2; HRMS(ESI)m / z calcd for C 13 H 13 N 2 O[M+H] + 213.1028,found 213.1038.

Embodiment 2

[0022] Example 2 A method for preparing urea compounds, using two methods to prepare the compound represented by formula I-b

[0023]

[0024] Method 1 The preparation steps are as follows: In the air, add magneton, substituted oxazolone (0.3mmol), sodium acetate (0.3mmol) and methanol (1mL) into a 10mL round bottom flask, and add aniline under stirring. (0.3mmol). Then plug the rubber stopper and heat and stir in an oil bath at 60°C for 2h. After the reaction is completed, petroleum ether / ethyl acetate is selected as the mobile phase, and the product is purified by flash silica gel column chromatography.

[0025] Method 2 The preparation steps are as follows: In the air, add magneton, 3-phenyl-1,4,2-dioxazol-5-one (0.3mmol), sodium acetate (0.3mmol) to a 10mL round bottom flask. mmol) and methanol (1 mL), and add substituted amine (0.3 mmol) under stirring. Then plug the rubber stopper and heat and stir in an oil bath at 60°C for 2h. After the reaction is completed, petroleum ...

Embodiment 3

[0027] Example 3 A method for preparing urea compounds, using two methods to prepare the compound represented by formula I-c

[0028]

[0029] Method 1 The preparation steps are as follows: In the air, add magneton, substituted oxazolone (0.3mmol), sodium acetate (0.3mmol) and methanol (1mL) into a 10mL round bottom flask, and add aniline under stirring. (0.3mmol). Then plug the rubber stopper and heat and stir in an oil bath at 60°C for 2h. After the reaction is completed, petroleum ether / ethyl acetate is selected as the mobile phase, and the product is purified by flash silica gel column chromatography.

[0030] Method 2 The preparation steps are as follows: In the air, add magneton, 3-phenyl-1,4,2-dioxazol-5-one (0.3mmol), sodium acetate (0.3mmol) to a 10mL round bottom flask. mmol) and methanol (1 mL), and add substituted amine (0.3 mmol) under stirring. Then plug the rubber stopper and heat and stir in an oil bath at 60°C for 2h. After the reaction is completed, petroleum ...

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PUM

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Abstract

The invention relates to a synthetic method of a urea compound, comprising the following steps: adding substituted oxazolone and sodium acetate into a methanol solution, and adding substituted amine under the stirring condition, reacting and carrying out column chromatography to obtain the urea compound. The defect that dangerous compounds need to be used during existing synthetic process is overcome, and a one-pot method is adopted to replace an existing reaction with low yield. The method of the invention has mild reaction condition, the operation is simple, raw materials are easily available, and the substrate can be converted into various other useful molecules. The compound has strong practicality, and can be applied to synthesis of the pesticide daimuron, dieresis long and the anti-cancer drug Sorafenib. The invention relates to a green and environmentally-friendly unsymmetrical urea compound synthesis method with simple process and low cost.

Description

Technical field [0001] The invention belongs to the field of organic compound synthesis methods, and relates to a synthesis method and application of urea compounds. Background technique [0002] Asymmetric urea derivatives have become commonly used chemicals in the chemical industry, including pesticides, dyes, polymers, organic catalysts and drugs. Asymmetrically substituted phenyl ureas such as diuron, diuron, and thidiazuron show broad-spectrum herbicidal activity as herbicides. In the pharmaceutical field, asymmetric N,N'-diarylurea has a variety of biological applications, including anticonvulsant, antibacterial, antiviral and anti-inflammatory. In addition, due to their outstanding multiple kinase inhibitory activities, these asymmetric ureas have received attention in the development of anti-cancer drugs. The aryl urea part plays an important role as a key binding scaffold for the hydrophobic pocket of the kinase domain through hydrogen bonding and hydrophobic interactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/00C07C273/18C07C275/28C07C275/30C07C275/34C07C275/42C07C275/64C07C319/12C07C323/44C07D209/14C07D209/40C07D209/88C07D213/40C07D213/75C07D213/81C07D307/66C07D317/58C07D333/36
Inventor 邹宏斌苏帕卡清迈张金泉
Owner ZHEJIANG UNIV
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