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Synthesis method of S-substituted-anthranilate thioester derivatives

A technology of aminobenzoic acid thioester and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of high risk factor, limited promotion, high volatility, etc., and achieve the effects of environmental friendliness, simple and safe operation, and less three wastes

Inactive Publication Date: 2013-01-30
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method uses p-methylthiophenol, which is highly toxic, volatile, and has a foul smell, as a raw material, which requires high equipment and has a high risk factor in the production process.
Therefore, the generalization of these methods mentioned above is limited

Method used

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  • Synthesis method of S-substituted-anthranilate thioester derivatives
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  • Synthesis method of S-substituted-anthranilate thioester derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Disulfide, isatoic anhydride compounds, accelerators and basic compounds are fed in a molar ratio of 1.0:2.5:4.0:3.0, the disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The red acid anhydride compound is isatoic anhydride, and the feeding quality is 40.7g (0.25mol); the accelerator is sodium dithionite, and the feeding quality is 69.6g (0.4mol); the basic compound is potassium carbonate, and the feeding quality is 41.4g (0.3mol); The organic solvent is 218 g of dimethyl sulfoxide, and its total consumption is 10 times of the mass of diphenyl disulfide.

[0032] Dissolve isatoic anhydride and accelerator in an organic solvent (the amount of organic solvent is 6 times the mass of diphenyl disulfide). Dissolve diphenyl disulfide and potassium carbonate in an organic solvent (the amount of organic solvent is 4 times the mass of diphenyl disulfide), slowly add dropwise to the solution of isatoic anhydride and accelerator, and the reaction tempera...

Embodiment 2

[0036] Disulfide, isatoic anhydride compounds, accelerators and basic compounds are fed in a molar ratio of 1.0:2.5:4.0:3.0, the disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The red acid anhydride compound is isatoic anhydride, and the feeding mass is 40.7g (0.25mol); The solvent is 218 g of dimethyl sulfoxide, and its total consumption is 10 times the mass of diphenyl disulfide.

[0037]All the other are the same as in Example 1, the resulting product S-phenylanthranilic acid thioester 14.2g, yield 62%, purity 97.5%.

Embodiment 3

[0039] Disulfide, isatoic anhydride compounds, accelerators and basic compounds are fed in a molar ratio of 1.0:2.5:4.0:3.0, the disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The red acid anhydride compound is isatoic anhydride, and the feeding quality is 40.7g (0.25mol); the accelerator is sodium dithionite, and the feeding quality is 69.6g (0.4mol); the basic compound is potassium carbonate, and the feeding quality is 41.4g (0.3mol); The organic solvent is 218 g of N,N,-dimethylformamide, the total amount of which is 10 times the mass of diphenyl disulfide.

[0040] The rest are the same as in Example 1, and the resulting product S-phenyl anthranilate thioester is 17.9g, with a yield of 78% and a purity of 97.9%.

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Abstract

The invention discloses a synthesis method of S-substituted-anthranilate thioester derivatives disclosed as Formula (I), which comprises the following steps: sufficiently reacting isatoic anhydride compounds disclosed as Formula (II) and dithioether compounds disclosed as Formula (III) in an inert organic solvent at 0-120 DEG C in the presence of an accelerator and basic compounds; and after the reaction finishes, separating and purifying the reaction solution to obtain the S-substituted-anthranilate thioester derivatives disclosed as Formula (I). The method disclosed by the invention has the advantages of reasonable technological conditions, simple and safe operation, mild reaction conditions, high reaction yield, cheap and accessible raw materials, environment-friendly substrate, low production cost and fewer three wastes.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of S-substituted anthranilic acid thioester derivatives. (2) Background technology [0002] Thioester derivatives are natural compounds with multifunctional uses. Due to their special structure, some compounds have pharmacological activity. They are also widely used in medicine, pesticides and other aspects. At the same time, thioester derivatives are also an important class of intermediates in organic synthesis. Therefore, the synthesis of thioester derivatives is of great significance in organic synthesis. However, as far as we know, there are only two examples of preparation methods of S-substituted anthranilate thioesters (such as J. Org. Chem. 1959, 24, 1214 and Tetrahedron Lett. 2010, 51, 5368). These reports all use the reaction of isatoic anhydride and thiophenol to synthesize S-substituted anthranilic acid thioesters. However, this method uses p-methylthiophenol which is highly toxic,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/26
Inventor 陈久喜吴华悦刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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