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A kind of method for preparing diaromatic ring substituted olefin

An aromatic ring and aromatic technology, which is applied in the preparation of carboxylic acid nitriles, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of a large number of catalysts, harsh reaction conditions, catalyst recovery and mechanical application, and large-scale promotion and use.

Active Publication Date: 2016-11-02
辽宁昊维科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, the Knoevenagel condensation reaction uses organic bases or their corresponding salts as catalysts, but the recovery and application of catalysts limit large-scale promotion and use
In recent years, many catalysts have emerged, such as: MgO / ZnO, amine-functionalized polyacrylonitrile fiber, La 2 o 3 / MgO,Ni-SiO 2 ,Si-MCM-41supported basicmaterials and IRMOF-3, etc., although these methods have achieved some success, but there are some defects in them, such as: low reaction yield, need a large amount of catalyst, narrow substrate scope, Harsh reaction conditions, and the use of some toxic solvents such as dichloromethane

Method used

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  • A kind of method for preparing diaromatic ring substituted olefin
  • A kind of method for preparing diaromatic ring substituted olefin
  • A kind of method for preparing diaromatic ring substituted olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Thiphenaldehyde (5mmol), 2-cyanomethylbenzimidazole (5mmol), 0.735g catalyst, and water (10mL) were sequentially added into a 50mL three-neck flask, stirred at room temperature for 2 hours, and detected by TLC, the raw materials basically disappeared. The catalyst was collected, the reaction solution was poured out, filtered, and the obtained solid was recrystallized with ethanol to obtain the product with a yield of 79% and a content of 98%.

[0025] 2-(1H-benzoimidazol-2-yl)-3-(thiophen-2-yl)acrylonitrile: 1 H NMR (400MHz, CDCl 3 ):δ7.15-7.22(m,1H),7.30-7.37(m,2H),7.50-7.52(m,1H),7.66-7.70(m,2H),7.76-7.77(m,1H),7.87 -7.89(m,1H),8.63(s,1H); 13 CNMR (100MHz, CDCl 3 ): δ98.1, 115.6, 115.7, 116.7, 123.6, 129.1, 134.5, 136.8, 137.0, 139.3, 147.6

Embodiment 2

[0027] Thiphenaldehyde (5mmol), 2-cyanomethylbenzimidazole (5mmol), 0.147g catalyst, and water (10mL) were sequentially added into a 50mL three-neck flask, stirred at room temperature for 5 hours, and detected by TLC, the raw materials basically disappeared, and an external magnetic field was applied to absorb The catalyst was collected, the reaction solution was poured out, filtered, and the obtained solid was recrystallized with ethanol to obtain the product with a yield of 62% and a content of 97%.

Embodiment 3

[0029] Thiphenaldehyde (5mmol), 2-cyanomethylbenzimidazole (6mmol), 0.147g catalyst, and water (10mL) were sequentially added into a 50mL three-neck flask, stirred at room temperature for 3 hours, and detected by TLC, the raw materials basically disappeared, and an external magnetic field was applied to absorb The catalyst was collected, the reaction solution was poured out, filtered, and the obtained solid was recrystallized with ethanol to obtain the product with a yield of 76% and a content of 99%.

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Abstract

The invention relates to an efficient environment-friendly catalyst, and a new method for preparing double-(hetero)aromatic-ring substituted alkene under a room-temperature condition by taking water as a reaction medium. The method comprises: taking n-propylamine supported by super-paramagnetism nanometer particles and modified by ion atmosphere as a catalyst, and under the conditions of room temperature, normal pressure and water reaction medium, performing Knoevenagel condensation reaction on an (hetero)aromatic-ring substituted active alkene substance and an aromatic aldehyde, so as to obtain a corresponding double-(hetero)aromatic-ring substituted alkene derivative. The reaction yield is not obviously reduced after the supported catalyst is repeatedly used for 8 times. The method is simple in operation, high in yield, simple in catalyst recovery, good in reusability of the catalytic reaction system and mild in reaction conditions, and has good industrialization prospect.

Description

technical field [0001] The invention relates to a high-efficiency, green method for preparing diaromatic ring-substituted olefins through Knoevenagel condensation using novel superparamagnetic nano-loaded and ionic liquid-modified n-propylamine as a catalyst under the condition of using water as a solvent. technical background [0002] The Knoevenagel condensation reaction of reactive methylene compounds and aromatic aldehydes has become one of the important reactions for carbon-carbon formation in the field of organic synthesis. The condensation products are abstracted olefins, which can be used as precursor raw materials for Michael reaction, "one-pot cooking" reaction and continuous reaction in organic synthesis, and are also important intermediates for the preparation of functional polymers, fine chemicals and chemical raw materials. Generally, organic bases or their corresponding salts are used as catalysts in the Knoevenagel condensation reaction, but the recovery and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06C07D235/16C07D277/64C07C255/35C07C253/30C07D209/18B01J31/28
CPCB01J31/28C07C253/30C07D209/18C07D235/16C07D277/64C07D409/06C07C255/35
Inventor 应安国杨健国倪宇翔胡华南
Owner 辽宁昊维科技有限公司
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