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6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate and synthetic method thereof

A technology of benzothiazole and aminomethyl, which is applied in the field of organic drug synthesis, can solve the problems of low yield and cumbersome synthesis methods, and achieve the effects of high yield, reduced production cost, 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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  • 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate and synthetic method thereof
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  • 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] This example provides a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate, which is Intermediate 3: 2-(1,1-dioxo -1,2-Benzothiazol-3-on-6-ylmethyl)-1H-isoindole-1,3-dione. The synthesis method of the intermediate 3 comprises the steps of: synthesizing the intermediate 4, synthesizing the intermediate 5, synthesizing the intermediate 6 and synthesizing the intermediate 3. The preparation of intermediates formed by each step is shown below.

[0047] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0048] The synthetic method of described intermediate 4 comprises the following steps:

[0049] Synthesis of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione Weigh 7g of p-methylbenzyl chloride and dissolve it with an appropriate amount of N,N-dimethylformamide, and add it to the system successively Add 7.35g of phthalimide, 8.1g of tetrabutylammonium bromide and 5.3g of sodium carbonate, and react at 50°C for 2h; after the reaction, extract with wat...

Embodiment 2

[0071] This example provides a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate, which is Intermediate 3: 2-(1,1-dioxo -1,2-Benzothiazol-3-on-6-ylmethyl)-1H-isoindole-1,3-dione. The synthesis method of the intermediate 3 comprises the steps of: synthesizing the intermediate 4, synthesizing the intermediate 5, synthesizing the intermediate 6 and synthesizing the intermediate 3. The preparation of intermediates formed by each step is shown below.

[0072] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0073] The synthesis method of intermediate 4 in this example is basically the same as the synthesis method of intermediate 4 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 ...

Embodiment 3

[0085] This example provides a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate, which is Intermediate 3: 2-(1,1-dioxo -1,2-Benzothiazol-3-on-6-ylmethyl)-1H-isoindole-1,3-dione. The synthesis method of the intermediate 3 comprises the steps of: synthesizing the intermediate 4, synthesizing the intermediate 6 and synthesizing the intermediate 3. The preparation of intermediates formed by each step is shown below.

[0086] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0087] The synthesis method of intermediate 4 in this example is basically the same as the synthesis method of intermediate 4 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 r...

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Abstract

The invention provides a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate. The chemical name of the intermediate is 2-(1,1-dioxo-1,2-benzothiazol-3-keto-6-ylmethyl)-1H-isoindole-1,3-dione,and the structural formula of the intermediate is shown in the specification (intermediate 3). The invention further provides a synthetic method of the 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate. The intermediate 3 provided by the invention provides a novel method and a novel synthetic route for synthesizing a mesosulfuron-methyl intermediate that is 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one. The novel synthetic route does not need hydrogenation reduction reaction, mainly comprises substitution reaction and oxidation reaction, is mild in reaction condition, easily available in various raw materials and high in yield, can effectively reduce the production cost, and has a relatively strong industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic drug synthesis, and specifically relates to a 6-aminomethyl-1,1-dioxo-1,2-benzothiazol-3-one intermediate and a synthesis method thereof. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C07D209/48C07D275/06
CPCC07D417/06C07D209/48C07D275/06
Inventor 邓照西
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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