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Synthesis method and application of compound

A synthesis method and compound technology are used in the synthesis of methyl 2-benzene-1,3,5-tricarboxylate and the synthesis of pesticide intermediate impurities, which can solve the problems of low reaction yield and the like, and achieve a simple operation process. Effect

Active Publication Date: 2019-01-18
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In the third step condensation reaction in this route, it was found that the reaction yield was low, accompanied by impurities. After separation and structural characterization, it was determined that one of the impurities was 2-(1,3-dimethoxy-3-oxo Prop-1-en-2-yl)methyl benzene-1,3,5-tricarboxylate, there is no report on the synthesis and structure of this impurity in the previous literature

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  • Synthesis method and application of compound

Examples

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Embodiment 1

[0048] Example 1 Synthetic method of 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylic acid methyl ester

[0049]Add 540g of sodium methoxide into the reaction vessel at room temperature, add 1160g of methyl 3-methoxyacrylate into the reaction vessel, start stirring for about 10 minutes, add 8L of solvent DMAC, heat to the reaction temperature of 35°C, and react for 2.5 hours. After the reaction was completed, the reaction solution was added into ice water with 4 times the amount of solvent (by volume), stirred for 20 min, and solids were precipitated and filtered. The filtrate was extracted with ethyl acetate, and the organic phase was rotary evaporated. After cooling at low temperature, a white solid precipitated, and filtered to obtain methyl 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylate. For its related detection spectrum, see figure 1 - Figure 10 .

Embodiment 2-9

[0050] Example 2-9 Synthetic method of 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylic acid methyl ester

[0051] Examples 2 to 9 are respectively a synthesis method of 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylic acid methyl ester , their operating steps are all similar to those in Example 1, only the type and amount of the reactant, and the control parameters in the process, the yield of the product, etc. are different, specifically see the following table:

[0052]

Embodiment 10

[0053] Example 10 Application of methyl 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylate

[0054]

[0055] In the process of synthesizing the intermediate of flonicamid by the method of the above formula, the impurity 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3 , 5-methyl tricarboxylate, and the presence of impurities will not only affect the quality of intermediates and final products, but also greatly reduce the yield of the reaction.

[0056] In this example, 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylic acid methyl ester prepared in Example 1-9 Provides an application that can be used as a standard reference substance to detect flonicamid and its intermediate N-(2-methoxycarbonylvinyl)-4,4,4-trifluoro-3-one-1-butan Whether and how much methyl 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene-1,3,5-tricarboxylate exists in enamine. In addition, in the process of synthesizing the intermediate of flonicamid with the above method, it ca...

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Abstract

The invention discloses a synthesis method and application of a compound. The compound is 2-(1,3-dimethoxy-3-oxoprop-1-ene-2-yl)benzene-1,3,5-methyl triformate. According to the synthesis method of the compound, 3-methoxy acrylate is taken as a raw material, is subjected to four-molecule condensation reaction under base catalysis, and then is cyclized under this condition to form the 2-(1,3-dimethoxy-3-oxoprop-1-ene-2-yl)benzene-1,3,5-methyl triformate as an end product. The synthesis method provided by the invention has a simple and safe operation process, and the product yield is 30%; the end product can be used as a standard product for detecting and monitoring a synthesis process of a pesticide flonicamid.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a method for synthesizing pesticide intermediate impurities, specifically a 2-(1,3-dimethoxy-3-oxoprop-1-en-2-yl)benzene -Synthetic method and application of methyl 1,3,5-tricarboxylate. Background technique [0002] In the process of drug synthesis, the formation of impurities will not only have a huge impact on the synthesis reaction and affect the yield of the product, but also directly or indirectly affect the quality of the drug, and therefore also affect the application of the drug. Effective monitoring of impurities in the synthesis process plays a key role in ensuring product yield and reducing the impact of impurities on drug effectiveness. [0003] Flunicamid (flonicamid or flunicotamid), the chemical name is N-cyanomethyl (trifluoromethyl) nicotinamide; the chemical formula is C 9 h 6 f 3 N 3 O. The structural formula is as follows: [0004] [0005] Flunicamid is a new...

Claims

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Application Information

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IPC IPC(8): C07C69/76C07C67/333C07C67/52C07C67/343C07C69/734G01N21/33G01N30/02
CPCC07C67/333C07C67/343C07C67/52G01N21/33G01N30/02G01N2030/027C07C69/734C07C69/76
Inventor 张越吴晓东冯雪肖园王泽昊陈爱兵
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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