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A kind of tandem synthesis method of 2-(phenylmethylene) malononitrile or its derivatives

A technology of phenylmethylene and synthetic methods, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid nitrile, etc., can solve the problems of low yield, long reaction time, complicated separation of catalysts and products, etc. To achieve the effect of high reactivity, short reaction time and cheap catalyst

Active Publication Date: 2021-12-31
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional synthesis methods for this class of compounds are usually carried out in batch reactors, which have several limitations, such as long reaction times, low yields, complex separation of catalysts and products, etc.

Method used

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  • A kind of tandem synthesis method of 2-(phenylmethylene) malononitrile or its derivatives
  • A kind of tandem synthesis method of 2-(phenylmethylene) malononitrile or its derivatives
  • A kind of tandem synthesis method of 2-(phenylmethylene) malononitrile or its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 2- (phenylmethylene) malononitrile (structural formula below):

[0031]

[0032] The mixture 3.3mmol benzaldehydedimethylacetal 3.8mmol malononitrile and diluted with ethyl acetate to 10mL, and then the resultant solution at a flow rate 0.5mL / min pressure injected into the HPLC column (the PS-piperazine 0.8-1.0g piperazine-1-sulfonic acid and PS- 0.8-1.0g), while the HPLC column was immersed in an oil bath at 50 deg.] C. After completion of the reaction, HPLC column rinsed with ethyl acetate, the product was collected, the solvent was evaporated, recrystallized from ethanol, to give solid product, 94% yield.

[0033] Compared with the compound prepared by conventional routes, the presence of a catalyst the method cheap, highly reactive, short reaction time, can be obtained without separation of the intermediate product and the product yield advantages. Melting point of the compound, IR and NMR characterized as follows: m.p.84.0-84.4 ℃; FT-IR (KBr, cm -1 )...

Embodiment 2

[0035] (E) -2- cyano-3-phenyl acrylate (structural formula below):

[0036]

[0037] The diluted 3.3mmol benzaldehydedimethylacetal with a nitrile compound mixed with ethyl acetate to ethyl acetate 3.8mmol 10mL, then the resulting solution at a flow rate 0.5mL / min pressure injected into the HPLC column (the PS-piperazine 0.8 PS- -1.0g and piperazine-1-sulfonic acid 0.8-1.0g), while the HPLC column was immersed in an oil bath at 50 deg.] C. After completion of the reaction, HPLC column rinsed with ethyl acetate, the product was collected, the solvent was evaporated, recrystallized from ethanol, to give solid product, 86% yield.

[0038] Compared with the compound prepared by conventional routes, the presence of a catalyst the method cheap, highly reactive, short reaction time, can be obtained without separation of the intermediate product and the product yield advantages. Melting point of the compound, IR and NMR characterized as follows: m.p.49.0-50.2 ℃; FT-IR (KBr, cm -1 ): 3...

Embodiment 3

[0040] Preparation of 2- (4-methoxy-methylene) malononitrile (structural formula below):

[0041]

[0042] The mixture was methoxybenzaldehyde dimethyl acetal 3.3mmol 3.8mmol of malononitrile and diluted with ethyl acetate to 10mL, and then the resultant solution at a flow rate 0.5mL / min pressure injected into the HPLC column (the PS-piperazine and 0.8 to 1.0 g PS- piperazine-1-sulfonic acid 0.8-1.0g), while the HPLC column was immersed in an oil bath at 50 deg.] C. After completion of the reaction, HPLC column rinsed with ethyl acetate, the product was collected, the solvent was evaporated, recrystallized from ethanol, to give solid product, 95% yield.

[0043] Compared with the compound prepared by conventional routes, the presence of a catalyst the method cheap, highly reactive, short reaction time, can be obtained without separation of the intermediate product and the product yield advantages. Melting point of the compound, IR and NMR characterized as follows: m.p.115.1-11...

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Abstract

The invention discloses a tandem synthesis method of 2-(phenylmethylene) malononitrile or its derivatives, the structural formula of the 2-(phenylmethylene) malononitrile or its derivatives is wherein, R 1 is hydrogen, p-methoxy, 2-bromine, 3-bromine or 4-bromine, R 2 For cyano or ester group. The present invention has synthesized a kind of chlorine ball acid-base functionalization catalyst, and successfully applied in series reaction to flow chemistry, and synthesized 2-(phenylmethylene) malononitrile or derivatives thereof at the gram level, compared with traditional test tubes Compared with the reaction, the reaction time is greatly reduced, the yield and product purity are improved, and the separation process of the catalyst and the product is avoided.

Description

Technical field [0001] The present invention belongs to the technical field of organic synthesis, particularly relates to a method for the synthesis of a series of 2- (phenylmethylene) malononitrile or a derivative thereof. Background technique [0002] As a method of growing the carbon chain may be introduced and an unsaturated carbon-carbon double bond, 2- (phenylmethylene) malononitrile synthesis reaction or its derivative has a very important role in organic synthesis. In recent years, 2- (phenylmethylene) malononitrile or a derivative thereof has been widely used in organic synthesis of drugs, natural products, fine chemicals and heterocyclic compounds such as, for example: anticoagulant coumarin synthetic, synthetic drugs sedative barbiturates and derivatives prepared antimalarial lumefantrine taken. However, the conventional method of synthesis of such compounds is usually carried out in a batch reactor, but there are several limitations, such as long reaction time, low yi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/34C07C253/30C07C255/41C07C255/37C07C255/35
CPCC07C255/34C07C255/41C07C255/37C07C255/35
Inventor 熊兴泉廖旭
Owner HUAQIAO UNIVERSITY
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