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A kind of preparation method of 5-aryl methylene rhodanine derivatives and non-imidazolium acidic ionic liquid catalyst for its preparation

A technology of aryl methylene and ionic liquid, which is applied in the field of chemical material preparation, can solve the problems of less recyclable times, large amount of catalyst usage, and complicated preparation process, so as to reduce the preparation cost, improve the utilization rate of raw materials, and improve the catalytic activity. high effect

Active Publication Date: 2019-05-17
东营睿港投资服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to overcome the shortcomings of existing 5-arylmethylene rhodanine derivatives preparation techniques, such as large amount of catalyst used, less recyclable times, complex preparation process, high cost, and easy to cause environmental pollution, providing A preparation method of 5-arylmethylene rhodanine derivatives and non-imidazolium-based acidic ionic liquid catalysts for their preparation

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  • A kind of preparation method of 5-aryl methylene rhodanine derivatives and non-imidazolium acidic ionic liquid catalyst for its preparation
  • A kind of preparation method of 5-aryl methylene rhodanine derivatives and non-imidazolium acidic ionic liquid catalyst for its preparation
  • A kind of preparation method of 5-aryl methylene rhodanine derivatives and non-imidazolium acidic ionic liquid catalyst for its preparation

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Experimental program
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Effect test

Embodiment 1

[0044] 1mmol benzaldehyde, 1mmol rhodanine and 0.07mmol non-imidazolium-based acidic ionic liquid were respectively added to 50ml one-necked bottles containing 6ml94% ethanol aqueous solution with a stirring bar and a condenser tube. React at 70°C for 6 minutes, track with TLC (thin plate chromatography), cool to room temperature after the reaction, crush the precipitated solid, let stand, filter with suction, wash the filter residue with 94% ethanol aqueous solution (3ml×3), and vacuum dry 5-benzylidene-2-mercaptothiazolidin-4-one was obtained with a yield of 96%. The filtrate was supplemented with 6ml of washing liquid, and benzaldehyde and rhodanine were directly added for repeated use. The remaining washing solution was used for the next washing after replenishing 9 ml with fresh ethanol aqueous solution.

[0045] The performance parameters of the 5-benzylidene-2-mercaptothiazolidin-4-one obtained in the present embodiment are: 1 H NMR (400MHz, DMSO-d 6 ): δ=7.62(s, 1H, ...

Embodiment 2～4

[0048] Take different reaction temperatures (shown in Table 1) to replace the reaction temperature described in Example 1, other conditions are the same as Example 1, and the experimental results are shown in Table 1.

Embodiment 5～7

[0054] Different molar amounts of non-imidazole-based acidic ionic liquid catalysts were used to replace the 0.07 mmol of non-imidazole-based acidic ionic liquid described in Example 1. Other conditions were the same as in Example 1. The experimental results are shown in Table 2.

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Abstract

The invention discloses a preparation method of a 5-aromatic methylene rhodanine derivative and a non-imidazolyl acidic ionic liquid catalyst for preparing the 5-aromatic methylene rhodanine derivative, and belongs to the technical field of preparation of chemical materials. In preparation reaction, the mole ratio of aromatic aldehyde to a rhodanine compound is 1 to 1; the mole use amount of the non-imidazolyl acidic ionic liquid catalyst is 7 to 10 percent of the molar weight of the aromatic aldehyde; the milliliter-based volume dose of an ethanol aqueous solution serving as a reaction solvent is 6 to 9 times the molar weight of the aromatic aldehyde; the reaction pressure is equal to atmospheric pressure, the reaction temperature is 70 to 82 DEG C, and the reaction time is 6 to 11 min. The preparation method comprises the following steps: after the reaction is completed, cooling the mixture to a room temperature, performing suction filtration, washing filtrate residues with the ethanol aqueous solution, and performing vacuum drying, namely obtaining the 5-aromatic methylene rhodanine derivative. Compared with the existing preparation method, the preparation method disclosed by the invention has the characteristics of small use amount of the catalyst, large number of recycling times, high reaction selectivity, short time and the like and is convenient for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of chemical material preparation, and in particular relates to a preparation method of 5-arymethylene rhodanine derivatives and a non-imidazole-based acidic ionic liquid catalyst for the preparation thereof. Background technique [0002] 5-Aromethylene rhodanine derivatives are an important class of nitrogen-containing heterocyclic compounds, which are widely used in industry, agriculture, pharmaceutical chemical industry, biological science and other fields. Among them, in the field of medicine, it has various biological activities such as antibacterial, analgesic, anticancer, and anticonvulsant, which can effectively inhibit the hydrolysis of β-lactam antibiotics by β-lactamase and improve the antibacterial effect of β-lactam antibiotic Activity, and at the same time, it is an intermediate for the preparation of important compound 5-substituted-4-thiazolidinone. Therefore, it is of great significance to s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07D277/36
CPCY02P20/584
Inventor 卢华沈智培沈建忠
Owner 东营睿港投资服务有限责任公司