2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative and synthesis method thereof

A technology of methyl benzyl and synthetic method, which is applied in the field of organic drug synthesis, can solve the problems of troublesome synthetic method and low yield, and achieve the effects of reduced production cost, high yield and mild reaction conditions

Active Publication Date: 2019-12-31
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

[0005] Among them, the precursor compound of the intermediate I mainly contains two kinds: 2-amino-4-aminomethylbenzoic acid methyl ester (compound 1

Method used

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  • 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative and synthesis method thereof
  • 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative and synthesis method thereof
  • 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0041] This embodiment provides the synthesis method of intermediate 4, intermediate 5, intermediate 6 and corresponding intermediates and the method of synthesizing compound 2 by using intermediate 4, intermediate 5 and intermediate 6.

[0042] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0043] The synthetic method of described intermediate 4 comprises the following steps:

[0044] 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 water, collect the organic layer and remove the solvent to obtain 12.3g of 2- (4-methylbenzyl)-1H-isoindole-1,3-dione;

[0045] Synthesis of Intermediate 4 Dissolve 12.3g of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione in chlorofo...

Embodiment 2

[0065]This embodiment provides the synthesis method of intermediate 4, intermediate 5, intermediate 6 and corresponding intermediates and the method of synthesizing compound 2 by using intermediate 4, intermediate 5 and intermediate 6.

[0066] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0067] 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 sodium hydroxide were sequentially added to the system, React at 100°C for 1 hour; after the reaction, extract with water, collect the organic layer and remove the solvent to obtain 12.1 g of 2-(4-methylbenzyl)-1H-isoindole-...

Embodiment 3

[0079] This embodiment provides intermediate 4, intermediate 6 and the corresponding intermediate synthesis method and the method of using intermediate 4 and intermediate 6 to synthesize compound 2.

[0080] Intermediate 4: 2-(3-Sulphono-4-methylbenzyl)-1H-isoindole-1,3-dione

[0081] 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 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 obtain 12.2g of 2-(4-methylbenzyl)-1H-isoindole-1,3- Diketone;

[0082] Dissolve...

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Abstract

The invention provides a 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative, wherein the structural formula is defined in the specification, and the group R1 in the structural formula is hydroxyl, chloro or amino. The invention further provides a synthesis method of the 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative. According to the invention, the 2-(4-methylbenzyl)-1H-isoindole-1,3-dionederivative can be used as the intermediate of 6-aminomethyl-1,1-dioxo-1,2-benzothiazole-3-one, the new method and the new synthetic route are provided in the synthesis of a mesosulfuron-methyl intermediate 6-aminomethyl-1,1-dioxo-1,2-benzothiazole-3-one, and the new synthetic route does not need hydrogenation reduction reaction, and has characteristics of mild reaction conditions, easily available raw materials, high yield, effectively reduced production cost and strong industrial application prospect.

Description

technical field [0001] The invention belongs to the field of organic medicine synthesis, and specifically relates to a 2-(4-methylbenzyl)-1H-isoindole-1,3-dione derivative 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 Ar...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 邓照西
Owner ZHENGZHOU INST OF CHIRAL DRUGS RES CO LTD
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