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Preparation method of substituted urea compound

A technology for substituted urea and compounds, which is applied in the field of preparation of substituted urea compounds, can solve the problems of low atom economy, high toxicity of intermediate products, and non-environmental protection, and achieve the advantages of wide source of raw materials, simple and easy operation methods, and reduced environment effect of influence

Active Publication Date: 2021-06-08
CENT SOUTH UNIV +1
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] The invention provides a preparation method of substituted urea compounds, the purpose of which is to solve technical problems such as high toxicity of raw materials and intermediate products in the preparation process of substituted urea, low atom economy, and environmental protection, and to provide a product with high yield and easy operation process. Simple, safe and environmentally friendly preparation method

Method used

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  • Preparation method of substituted urea compound
  • Preparation method of substituted urea compound
  • Preparation method of substituted urea compound

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Add 15.59 parts of tetrachloromethane (99.0% content) into a reactor containing 85.00 parts of trifluorotoluene, add 38.01 parts of 1-tert-butoxycarbonylpiperazine (98.0% content), and then add 0.31 parts of trioxide Manganese (99.5%) and 32.48 parts of cesium carbonate (content is 99.9%), under xenon lamp as light source irradiation, after stirring reaction 10 hours, collect the chlorine that reaction process generates, the brown oily solution distillation that obtains is reclaimed trifluorotoluene solvent, A caramel-colored viscous 1,1'-carbonylbis(4-tert-butoxycarbonylpiperazine) liquid product was obtained.

[0044] After separation and purification of the obtained product, structural characterization was carried out by infrared spectroscopy and mass spectrometry. The results are as follows: figure 1 and figure 2 Shown:

[0045] The infrared spectrum of the 1,1'-carbonyl bis(4-tert-butoxycarbonylpiperazine) obtained in Example 1 is as follows: figure 1 As shown, i...

Embodiment 2

[0047] 15.54 parts of tetrachloromethane (content is 99.0%) are added in the reactor that 85.00 parts of benzotrifluoride are housed, add 20.23 parts of 1-methylpiperazine (content is 99.0%), then add 0.32 parts of trimanganese tetraoxide ( 99.5%) and 33.35 parts of cesium carbonate (content is 99.9%), under the irradiation of xenon lamp as the light source, after stirring for 10 hours, the chlorine gas generated in the reaction process was collected, and the obtained oily solution was distilled to reclaim the trifluorotoluene solvent to obtain light yellow Bis(4-methylpiperazin-1-yl)methanone solid product.

[0048] After separating and purifying the obtained product, the structure was characterized by infrared spectroscopy, the results are as follows: image 3 Shown:

[0049] The infrared spectrum of the two (4-methylpiperazin-1-yl) ketone that embodiment 2 obtains is as follows image 3 As shown, its main characteristic peaks are (cm -1 ): 3406.15 attributed to N-H stret...

Embodiment 3

[0051] 34.25 parts of tetrabromomethane (content is 97.0%) are added in the reactor that 85.00 parts of benzotrifluoride are housed, add 33.11 parts of 1-phenylpiperazine (content is 99.0%), then add 0.30 parts of trimanganese tetraoxide (99.5 %) and 32.07 parts of cesium carbonate (content is 99.9%), under xenon lamp as light source irradiation, stirring reaction after 10 hours, leave standstill layering, upper strata is yellow liquid, and lower stratum is the bromine simple substance of red black oily state, and supernatant solution is distilled The trifluorotoluene solvent was recovered to obtain a reddish-brown 1,1'-carbonylbis(4-phenylpiperazine) solid product.

[0052] After separating and purifying the obtained product, the structure was characterized by mass spectrometry, the results are as follows: Figure 4 Shown:

[0053] The mass spectrum of the 1,1'-carbonyl bis(4-phenylpiperazine) obtained in Example 3 is as follows Figure 4 As shown, the peak with a mass-to-c...

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Abstract

The invention provides a preparation method of a substituted urea compound. The preparation method comprises the following steps: taking a nitrogen-containing heterocyclic compound and tetrahalomethane as raw materials, carrying out illumination catalytic reaction in the presence of a catalyst and a solvent to prepare the substituted urea compound and a halogen simple substance; the preparation method is wide in raw material source, phosgene, triphosgene and the like which are high in toxicity are prevented from being adopted as raw materials, the influence of the preparation process on the environment is reduced, and the atom utilization rate of the reaction is increased; the reaction conditions are mild, the operation is simple and convenient, the environmental pollution is reduced, and the reaction cost is reduced; the product yield is high, the halogen simple substance is co-produced, the additional value is high, a large amount of waste is prevented from being generated, and the method has high atom economy and environment friendliness and is beneficial to application and popularization.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a preparation method of substituted urea compounds. Background technique [0002] Substituted ureas are an important class of fine chemicals, widely used in pesticides, herbicides, plant growth regulators and pharmaceutical intermediates, and can also be used as additives for petroleum, hydrocarbon fuels and polymers, such as corrosion inhibitors, anti Oxygen, anti-precipitation agent, etc. [0003] The synthesis methods of substituted ureas can be divided into two categories: isocyanate method and non-isocyanate method. The synthesis of substituted urea by isocyanate method is mainly to use phosgene, triphosgene, azide compound, etc. as raw materials to prepare isocyanate first, and then react with amine or amide compound to obtain substituted urea compound. Although phosgene is more practical as a raw material, the preparation of phosgene is also relatively easy, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/182C07D207/327C07D209/86C07D233/60C07D213/50
CPCC07D295/182C07D207/327C07D209/86C07D233/60C07D213/50
Inventor 马鑫邓兰青钟宏曹占芳费玲云王帅
Owner CENT SOUTH UNIV
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