Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof

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

Active Publication Date: 2019-08-06
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
  • Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof
  • Tandem synthesis method of 2-(phenylmethylene)malononitrile or derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of 2-(phenylmethylene) malononitrile (structural formula is as follows):

[0031]

[0032] The mixture of 3.3mmol benzaldehyde dimethyl acetal and 3.8mmol malononitrile was diluted to 10mL with ethyl acetate, and then the resulting solution was injected into the HPLC column at a flow rate of 0.5mL / min (PS-piperazine 0.8-1.0g and PS-piperazine-1-sulfonic acid 0.8-1.0 g), while immersing the HPLC column in a 50°C oil bath. After the reaction was completed, the HPLC column was washed with ethyl acetate, the product was collected, the solvent was evaporated, and recrystallized with ethanol to obtain a solid product with a yield of 94%.

[0033] Compared with the traditional route for preparing the compound, the method has the advantages of cheap and easy-to-obtain catalyst, high reaction activity, short reaction time, the product can be obtained without intermediate separation, and the product yield is high. The melting point, IR and NMR characteristics ...

Embodiment 2

[0035] (E) the preparation of -2-cyano-3-ethyl phenylacrylate (structural formula is as follows):

[0036]

[0037] Mix 3.3 mmol benzaldehyde dimethyl acetal with 3.8 mmol nitrile ethyl acetate and dilute to 10 mL with ethyl acetate, then inject the resulting solution into an HPLC column (PS-piperazine 0.8 -1.0g and PS-piperazine-1-sulfonic acid 0.8-1.0g), while immersing the HPLC column in a 50°C oil bath. After the reaction was completed, the HPLC column was washed with ethyl acetate, the product was collected, the solvent was evaporated, and recrystallized with ethanol to obtain a solid product with a yield of 86%.

[0038] Compared with the traditional route for preparing the compound, the method has the advantages of cheap and easy-to-obtain catalyst, high reaction activity, short reaction time, the product can be obtained without intermediate separation, and the product yield is high. The melting point, IR and NMR characteristics of the compound are as follows: m.p.4...

Embodiment 3

[0040] The preparation of 2-(4-methoxyphenylmethylene) malononitrile (structural formula is as follows):

[0041]

[0042] The mixture of 3.3mmol p-methoxybenzaldehyde dimethyl acetal and 3.8mmol malononitrile was diluted to 10mL with ethyl acetate, and then the resulting solution was injected into the HPLC column (PS-piperazine 0.8-1.0g and PS-piperazine-1-sulfonic acid 0.8-1.0g), while immersing the HPLC column in a 50°C oil bath. After the reaction was completed, the HPLC column was washed with ethyl acetate, the product was collected, the solvent was evaporated, and recrystallized with ethanol to obtain a solid product with a yield of 95%.

[0043] Compared with the traditional route for preparing the compound, the method has the advantages of cheap and easy-to-obtain catalyst, high reaction activity, short reaction time, the product can be obtained without intermediate separation, and the product yield is high. The melting point, infrared and NMR characteristics of th...

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PUM

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Abstract

A tandem synthesis method of 2-(phenylmethylene)malononitrile or a derivative thereof is disclosed. The general structural formula of the 2-(phenylmethylene)malononitrile or a derivative thereof is shown in the description, wherein R1 is hydrogen, p-methoxy, 2-bromo, 3-bromo or 4-bromo, and R2 is a cyano or ester group. A chloromethylated polystyrene microsphere acid-base functionalized catalyst is synthesized, a tandem reaction is successfully applied to the flow chemistry, and the 2-(phenylmethylene)malononitrile or a derivative thereof is synthesized in a gram scale. Compared with traditional test tube reactions, the method greatly reduces the reaction time, improves the yield and product purity, and avoids a step of separating a product from the catalyst.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a tandem synthesis method of 2-(phenylmethylene)malononitrile or derivatives thereof. Background technique [0002] As a method for extending carbon chains and introducing unsaturated carbon-carbon double bonds, the synthesis reaction of 2-(phenylmethylene)malononitrile or its derivatives plays a very important role in organic synthesis. In recent years, 2-(phenylmethylene)malononitrile or its derivatives have been widely used in the organic synthesis of drugs, natural products, fine chemicals and heterocyclic compounds, such as: anticoagulant coumarin Synthesis of sedative barbiturate derivatives and preparation of antimalarial drug lumefantrine. However, traditional synthesis methods for such compounds are usually carried out in batch reactors, which suffer from various limitations, such as long reaction times, low yields, and complicated separation of ca...

Claims

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Application Information

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Patent Type & Authority Applications(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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