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Synthesis method and application for trimethyl 1,3,5-benzene tricarboxylate

A technology of trimethylbenzenetricarboxylate and trimethyltricarboxylate, which is applied in the field of pharmacy, can solve the problems of long reaction time, failure to represent the separation yield, and the separation method provided by the reactant, so as to achieve the simple separation method and the operation process easily controlled effects

Active Publication Date: 2019-02-12
HEBEI LANSHENG BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The catalyst necessary for the reaction is a Lewis acid, which is similar to CeCl 3 , GdCl 3 , Yb(OTf) 3 , Sm(OTf) 3 , ZrCl 2 , InBr 3 Compounds such as 3, 4, 12, 13, 14, and 15 must contain metal elements of Group 3, 4, 12, 13, 14, and 15. In addition to the solvent, an auxiliary organic acid such as acetic acid needs to be added to the reaction. The reaction time is longer, generally 6 hours; After the end, waste water containing the above metal compounds will be produced, which will pollute the environment
Moreover, there is no clear separation method for the reactants in the literature, and the product yield is only based on gas phase detection, which cannot represent the real separation yield

Method used

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  • Synthesis method and application for trimethyl 1,3,5-benzene tricarboxylate
  • Synthesis method and application for trimethyl 1,3,5-benzene tricarboxylate
  • Synthesis method and application for trimethyl 1,3,5-benzene tricarboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1 A kind of synthetic method of 1,3,5-trimethylbenzenetricarboxylate

[0043] (1) Self-molecular condensation reaction

[0044] Add 4.3kg of sodium methoxide (base, as a catalyst) to 50L of solvent N,N-dimethylformamide (DMF) at 0°C, stir for 0.5h to disperse into a suspension, heat up to 25°C and add 10kg 3-methoxy methyl acrylate, after stirring for 0.5h, generate the intermediate state of 6-methoxy-1,3,5-hexatriene-1,3,5-tricarboxylic acid trimethyl ester;

[0045] (2) Cyclization reaction

[0046] Slowly raise the temperature to 35°C, and control the temperature at 35°C to continue the reaction for 3 hours. The intermediate state obtained in step (1) produces a reaction solution A. Add the reaction solution A to 200L of ice water, and adjust the pH to 6.52 with hydrochloric acid (adjust with a pH meter). Stirring was continued for 1 h until white flocculent solids were completely precipitated. Filter and dry to obtain 1,3,5-trimethyl benzenetricarboxyl...

Embodiment 2

[0047] Embodiment 2 A kind of synthetic method of 1,3,5-trimethylbenzenetricarboxylate

[0048] (1) Self-molecular condensation reaction

[0049] Add 4.3kg of sodium methoxide (base, as a catalyst) to 50L of solvent N,N-dimethylformamide (DMF) at 0°C, stir for 0.5h to disperse into a suspension, heat up to 25°C and add 10kg of methyl 3,3-dimethoxypropionate, stirred for 0.5h to generate the intermediate state of trimethyl 6-methoxy-1,3,5-hexatriene-1,3,5-tricarboxylate ;

[0050] (2) Cyclization reaction

[0051] Slowly raise the temperature to 35°C, and control the temperature at 35°C to continue the reaction for 3 hours. The intermediate state obtained in step (1) produces a reaction solution A. Add the reaction solution A to 200L of ice water, and adjust the pH to 6.52 with hydrochloric acid (adjust with a pH meter). Stirring was continued for 1 h until white flocculent solids were completely precipitated. Filter and dry to obtain 1,3,5-trimethyl benzenetricarboxylate. F...

Embodiment 3～8

[0052] Embodiment 3~8 1,3, the synthetic method of 5-benzene trimethyl carboxylate

[0053] Examples 3 to 8 are respectively a synthesis method of 1,3,5-trimethylbenzenetricarboxylate. The operation steps are the same as those in Example 1 and Example 2, except for the types and amounts of the reaction raw materials, and The reaction time, reaction temperature, pH value and other control parameters in the process are different, see the following table for details:

[0054]

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Abstract

The invention discloses a synthesis method for trimethyl 1,3,5-benzene tricarboxylate. Methyl 3-methoxyacrylate or methyl 3,3-dimethoxypropionate is taken as a raw material, and the raw material is subjected to self molecular condensation and cyclization reaction under a base catalysis condition to synthesize a target product. The invention also discloses the application of the trimethyl 1,3,5-benzene tricarboxylate, the trimethyl 1,3,5-benzene tricarboxylate can be taken as a standard substance for detecting and monitoring the synthesis of the pesticide flonicamid and the intermediate thereof. The synthesis method provided by the invention is simple in operation, intermediate condensation does not need to be separated, a product is obtained through one-pot type reaction, a process can beeasily controlled, and the yield of the obtained trimethyl 1,3,5-benzene tricarboxylate is 40%.

Description

technical field [0001] The invention belongs to the field of pharmacy and relates to a method for synthesizing an organic intermediate, in particular to a method for synthesizing 1,3,5-trimethylbenzenetricarboxylate and its application. Background technique [0002] In the process of drug synthesis, the formation of impurities will not only have a huge impact on the synthesis reaction, but also directly or indirectly affect the quality of the drug, and thus 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) is a new type of low-toxic pyridinamide insect growth regulator insecticide discovered by Ishihara Sangyo Co., Ltd. in Japan. The chemical name is N-cyanomethyl (trifluoromethyl) nicotinamide ; chemical formula is C 9 h 6 f 3 N 3 O. The structural formula is as follo...

Claims

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Application Information

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IPC IPC(8): C07C67/327C07C69/76G01N30/02
CPCC07C67/327G01N30/02C07C69/76
Inventor 冯雪肖园吴晓东张越陈爱兵
Owner HEBEI LANSHENG BIOTECH CO LTD
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