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Synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one

A technology of benzothiazole and aminomethyl, which is applied in the field of organic drug synthesis, can solve problems such as troublesome synthesis methods and low yields, and achieve the effects of reducing production costs, high yields and mild reaction conditions

Active Publication Date: 2019-11-22
ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Among them, the precursor compound of the intermediate I mainly contains two kinds: 2-amino-4-aminomethylbenzoic acid methyl ester (compound 1) or 6 -Aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one (compound 2), the synthesis method of compound 2 is troublesome at present, and the yield is low

Method used

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  • Synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one
  • Synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one
  • Synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one

Examples

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Embodiment 1

[0044] This example provides a synthetic method for 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one, including sequentially synthesizing compound 6, compound 5, compound 4, compound 3 and the target Compound steps. The specific synthesis method of each compound is shown below.

[0045] Synthesis of compound 6: 2-(3-sulfo-4-methylbenzyl)-1H-isoindole-1,3-dione

[0046] Weigh 7g of p-methylbenzyl chloride and dissolve it with an appropriate amount of N,N-dimethylformamide, and then add 7.35g of phthalimide, 8.1g of tetrabutylammonium bromide and 5.3g of sodium carbonate to the system , reacted at a temperature of 50° C. for 2 hours; after the reaction was completed, extracted with water, collected the organic layer and removed the solvent to obtain 12.3 g of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione;

[0047] Dissolve 12.3g of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione in chloroform, then add 8.7g of chlorosulfonic acid, and react at 80°C for 3h; after the reaction, wash with ...

Embodiment 2

[0067] This example provides a synthetic method for 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one, including sequentially synthesizing compound 6, compound 5, compound 4, compound 3 and the target Compound steps. The synthesis method of each compound provided in this example is basically the same as that of the corresponding compound provided in Example 1.

[0068] Synthesis of compound 6: 2-(3-sulfo-4-methylbenzyl)-1H-isoindole-1,3-dione

[0069] The method for synthesizing compound 6 in this example is basically the same as the method for synthesizing compound 6 provided in Example 1, the main difference is that the reaction solvent, basic catalyst and reaction parameters are different. Specifically, in this example, 7g of p-methylbenzyl chloride was weighed and dissolved with an appropriate amount of pyridine, and 7.35g of phthalimide, 16g of tetrabutylammonium bromide and 6g of sodium hydroxide were sequentially added to the system, React at 100°C for 1 hour; after th...

Embodiment 3

[0081] This example provides a synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one, including the steps of sequentially synthesizing compound 6, compound 4, compound 3 and the target compound . The specific synthesis method of each compound is shown below.

[0082] Synthesis of compound 6: 2-(3-sulfo-4-methylbenzyl)-1H-isoindole-1,3-dione

[0083] The method for synthesizing compound 6 in this example is basically the same as the method for synthesizing compound 6 provided in Example 1, the main difference is that the reaction solvent, basic catalyst and reaction parameters are different. Specifically, in this example, 7g of p-methylbenzyl chloride was weighed and dissolved with an appropriate amount of dimethyl sulfoxide, and 7.35g of phthalimide, 3.5g of tetrabutylammonium bromide and 6g of triethylamine was reacted at 70°C for 1.5h; after the reaction was completed, it was extracted with water, and the organic layer was collected to remove the solvent to ...

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Abstract

The invention provides a preparation method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one. The method comprises following steps of: synthesizing 2-(3-sulfo-4-methylbenzyl)-1H-isoindole-1,3-dione;2-(3-chlorosulfonyl-4-methylbenzyl)-1H-isoindole-1,3-dione; synthesizing 2-(3-aminosulfonyl-4-methylbenzyl)-1H-isoindole-1,3-dione; synthesizing 2-(1,1-dioxo-1,2-benzothiazol-3-keto-6-ylmethyl)-1H-isoindole-1,3-dione; and synthesizing the target compound. The synthetic method is a novel synthetic method of a mesosulfuron-methyl intermediate that is methyl 4-(methylsulfonamidomethyl)-2-sulfamoylbenzoate. The method does not need a hydrogenation reduction, reaction conditions are mild, various raw materials are easy to obtain, the yield is high, the production cost can be effectively reduced, and the method has a relatively strong industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic medicine synthesis, and in particular relates to a synthesis method of 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one. Background technique [0002] Methsulfuron-methyl, also known as Methsulfuron-methyl, chemical name 2-[(4,6-dimethoxypyrimidine 2-aminocarbonyl) aminosulfonyl]-a-(methylsulfonylamino) p-toluic acid Methyl ester is a new type of sulfonylurea herbicide developed by Bayer AG in 2002. Regarding sulfonylurea herbicides, it is the largest class of herbicides in the world. It mainly works by inhibiting acetolactate synthase , Weed roots and leaves absorb, and conduct in the plant body, thereby prompting weeds to stop growing to achieve the effect of weeding. The agent is mainly used to control gramineous weeds and some broad-leaved weeds in wheat fields, including okra, wild oats, clubhead grass, bluegrass, hardgrass, knotweed, sage grass, wheatgrass, shepherd's purse, sowgrass Artemisia and chic...

Claims

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Application Information

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IPC IPC(8): C07D275/06C07D209/48C07D417/06
CPCC07D275/06C07D209/48C07D417/06
Inventor 邓照西
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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