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Method for preparing cis-1-methoxycarbonyl-2-substituted phenyl-3,3-dinitrile cyclopropane under catalysis of niobium pentachloride

A technology of methoxycarbonylmethyltriphenylarsine bromide and niobium pentachloride, which is applied in the field of preparing cis-1-methoxycarbonyl-2-substituted phenyl-3,3-dinitrile cyclopropane to achieve easy The effect of separation and purification

Inactive Publication Date: 2013-12-11
YICHUN JINYANG NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is no report on the preparation of cis-1-methoxycarbonyl-2-substituted phenyl-3,3-dinitrile cyclopropane catalyzed by niobium pentachloride

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In this example, cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane was prepared according to the following steps:

[0029] (a) Control the mass ratio of methoxycarbonylmethyltriphenylarsine bromide: phenylmethylenemalononitrile: niobium pentachloride: methylene chloride to be 1:1:2:2;

[0030] (b) Put the raw materials weighed in step (a) into the reaction container at the same time, heat and stir until each component is fully dissolved, and react at a temperature of 0-40°C for 5-6 hours to obtain a reaction solution;

[0031] (c) Pour the reaction solution obtained after the reaction in step (b) into cold water, crystallize, filter, and dry to obtain cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane.

[0032] The product yield of the obtained cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane was 60%.

[0033] The nuclear magnetic data of the product prepared above is detected: 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 3.16 (d, J = 8.1 Hz, 1H, ...

Embodiment 2

[0035] In this example, cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane was prepared according to the following steps:

[0036] (a) Control the mass ratio of methoxycarbonylmethyltriphenylarsine bromide: phenylmethylenemalononitrile: niobium pentachloride: methylene chloride to be 1:2:2:4;

[0037] (b) Put the raw materials weighed in step (a) into the reaction container at the same time, heat and stir until each component is fully dissolved, and react at a temperature of 0-40°C for 5-6 hours to obtain a reaction solution;

[0038] (c) Pour the reaction solution obtained in step (b) into cold water, crystallize, filter, and dry to obtain cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane.

[0039] The product yield of the obtained cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane was 70%.

[0040] NMR data: 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 3.16 (d, J = 8.1 Hz, 1H, CH), 3.68 (d, J = 8.1 Hz, 1H, CH), 3.91 (s, 3H, OCH 3 ), 7.28 - 7.44 (m, 5H...

Embodiment 3

[0042] Follow the steps below to prepare cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane:

[0043] (a) Control the mass ratio of methoxycarbonylmethyltriphenylarsine bromide: phenylmethylenemalononitrile: niobium pentachloride: methylene chloride to be 1:2:2:4;

[0044] (b) Heat and stir the methoxycarbonylmethyltriphenylarsine bromide, phenylmethylenemalononitrile and dichloromethane to fully dissolve, then slowly add niobium pentachloride to react while heating and stirring , control the reaction temperature to be 0-40°C and the reaction time to be 3-4 hours to obtain a reaction solution;

[0045] (c) Pour the reaction solution obtained after the reaction in step (b) into cold water, crystallize, filter, and dry to obtain cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane. The product yield of the obtained cis-1-methoxycarbonyl-2-phenyl-3,3-dinitrile cyclopropane was 75%.

[0046] NMR data: 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 3.16 (d, J = 8.1 Hz, 1H, ...

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Abstract

The invention provides a method for preparing cis-1-methoxycarbonyl-2-substituted phenyl-3,3-dinitrile cyclopropane under the catalysis of niobium pentachloride. The niobium pentachloride is prepared in a solvent under the action of the catalyst niobium pentachloride by taking brominating methoxycarbonyl methyl triphenylarsine and aryl methylene malononitrile as raw materials. Compared with the traditional reaction system, the method provided by the invention has the characteristics of higher yield, more easiness for post processing, higher product purity, high yield, low energy consumption, and the like.

Description

technical field [0001] The invention relates to a method for preparing cis-1-methoxycarbonyl-2-substituted phenyl-3,3-dinitrile cyclopropane by catalyzing niobium pentachloride. technical background [0002] Because small ring compounds have a wide range of biological activities, coupled with their low toxicity, high efficiency, environmental friendliness, and diverse structural changes, they have become a hot spot in the development of pesticides today; It is also widely used as a precursor for the synthesis of various lead compounds, so the study of the synthesis of such compounds has important theoretical and practical value. [0003] Commonly used methods for synthesizing cyclopropane compounds are: 1. Metal-induced chlorinated hydrocarbon cyclopropane method, i.e. CH 2 I 2 / Zn-Cu or CH 2 I 2 / ZnEt 2 Addition to olefins; 2. Transition metal catalyzed diazo compound cyclopropane method. This method decomposes diazo compounds through metals, generates metal carbenes o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/46
Inventor 王常清易艳平
Owner YICHUN JINYANG NEW MATERIALS CO LTD
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