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Photochemical synthesis method of imidazolidine compound

A technology of photochemical synthesis and synthesis method, applied in the field of photochemical organic synthesis

Active Publication Date: 2019-10-25
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the strong oxidizing properties of titanium dioxide photogenerated holes and secondary free radicals, TiO in general aqueous phase 2 Semiconductor photocatalytic system directly triggers complete mineralization of organic matter

Method used

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  • Photochemical synthesis method of imidazolidine compound
  • Photochemical synthesis method of imidazolidine compound
  • Photochemical synthesis method of imidazolidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Mixed crystal P25 titanium dioxide and N-benzylidene benzylamine (PhCH=NCH 2 Ph) by 1:1 molar ratio (0.5mmol:0.5mmol) is added in the temperature-controlled transparent reaction bottle filled with methanol and temperature-controlled 25 ℃, so that the concentration of mixed crystal P25 titanium dioxide in the reaction system is 10g / L, the concentration of imine in the reaction system is 0.5mol / L, airtight and seal, pass in inert gas, make the inert gas pressure in the temperature-controlled transparent reaction bottle to be 0.01MPa, control the temperature to be 25 ℃ and stir for half an hour to make the sub The amine adsorption reached equilibrium, and then irradiated the temperature-controlled transparent reaction flask with a 300-watt xenon lamp and kept the temperature at 25 °C. After 24 hours of irradiation, the reaction was stopped, and the reaction product was separated by column chromatography. The reaction product was mainly shown in the following formula 1,3- ...

Embodiment 2

[0059] The anatase titanium dioxide and N-benzylidene benzylamine (PhCH=NCH 2Ph), ethanol is added in the temperature-controlled transparent reaction flask filled with acetonitrile at a molar ratio of 1:2:4 (0.25mmol:0.5mmol:1mmol) and the temperature is controlled at 25°C, so that anatase-type titanium dioxide is in the reaction system The concentration of ethanol in the reaction system is 1g / L, the concentration of ethanol in the reaction system is 2mol / L, the seal is closed, the inert gas is introduced, and the inert gas pressure in the temperature-controlled transparent reaction bottle is 0.01MPa, and the control temperature is 25 ℃ and Stir for half an hour to make the ethanol adsorption reach equilibrium, then irradiate the temperature-controlled transparent reaction flask with a 300-watt xenon lamp and keep the temperature at 25 °C, stop the reaction after 24 hours of irradiation, and separate the product by column chromatography. The reaction product is mainly shown in ...

Embodiment 3

[0062] The rutile titanium dioxide and N-benzylidenebenzylamine (PhCH=NCH 2 Ph), benzyl alcohol joins in the temperature-controlled transparent reaction flask filled with DMF by the molar ratio of 1:1:2 (0.5mmol:0.5mmol:1mmol), so that the concentration of rutile titanium dioxide in the reaction system is 2g / L, the concentration of imine in the reaction system is 0.5 mol / L, and the concentration of benzyl alcohol in the reaction system is 1 mol / L, airtightly seal the mouth, pass in inert gas, and make the inert gas pressure in the temperature-controlled transparent reaction bottle to be 0.01MPa, control the temperature to 25°C and stir for half an hour to make the adsorption of benzyl alcohol and imine reach equilibrium, then irradiate the temperature-controlled transparent reaction flask with sunlight and keep the temperature at 25°C, stop the reaction after 20 hours of irradiation, and separate the product by column chromatography , the reaction product is mainly 1,3-dibenz...

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Abstract

The invention belongs to the field of photochemical organic synthesis, and particularly relates to a photochemical synthesis method of an imidazolidine compound. The photochemical synthesis method comprises the step that alcohol reacts with imine in the presence of light and a photocatalyst to obtain the imidazolidine compound. According to the photochemical synthesis method of the imidazolidine compound, the alcohol and imine dissolved in an inert organic solvent are utilized to realize the reaction of synthesis of the imidazolidine compound from the green low-toxic alcohol and imine by controlling the reaction time under the action of the photocatalyst under the induction of ultraviolet light or visible light, and the imidazolidine compound can be obtained. Moreover, the product of the photochemical synthesis method has high yield and good selectivity. The separation yield of the product is up to more than 95% and the selectivity is up to more than 99%. In addition, a preparation process is simple, the product can be obtained by one-step reaction, and the photochemical synthesis method is economical and environmentally friendly, and convenient to operate, and has high practicability.

Description

technical field [0001] The invention belongs to the technical field of photochemical organic synthesis, and in particular relates to a photochemical synthesis method of imidazolidine compounds. Background technique [0002] In industry, imidazolidine compounds are widely used as important chemical intermediates and products in pharmaceuticals, pesticides and herbicides. Moreover, the imidazolidine structural unit has important applications in ligand prosthetic groups of transition metal catalysts and organic small molecule catalysts. Its traditional preparation method is obtained through the condensation of 1,2-diamine and formaldehyde, and the extensive use of formaldehyde will cause serious environmental pollution. Recently, complexes of transition metal Lewis acid catalysts such as Ag and Cu can realize the construction of imidazolidines by the 1,3-dipolar cycloaddition reaction of electron-deficient methyleneamine ylides and imines. Enantioselectivity and even certain ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/02
CPCC07B2200/13C07D233/02
Inventor 马东阁刘阿楠张泽王谊
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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