Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 2-amino-4-methanesulfonamide methylbenzoate

A technology of methyl methanesulfonamide methyl benzoate and methyl formamido benzoate is applied in the field of preparation of methyl 2-amino-4-methanesulfonamide methyl benzoate, and can solve the problem of development of methanesulfonamide And the promotion obstacles, difficulty in mass production, affecting product development and other problems, to achieve the effect of stable process, less by-products, and less pollution

Active Publication Date: 2014-01-22
ZHEJIANG DINGLONG TECH +1
View PDF7 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein the preparation route of 4-cyano-2-nitrobenzoic acid methyl ester is 4-cyanotoluene through nitration, oxidation, esterification three steps, because raw material 4-cyanotoluene needs to use cyanide, raw material toxicity, production The safety control and waste water and waste liquid in the process pollute the environment greatly, so the raw material is difficult to obtain; 4-methyl-3-nitrobenzonitrile is obtained by nitration of 4-cyanotoluene and then passed through potassium dichromate / sulfuric acid System oxidation obtains 4-cyano-2-nitrobenzoic acid, and the yield reported in the literature is 46%, and the yield is relatively low; simultaneously, this step oxidation has serious exothermic heat in the reaction process due to the adoption of potassium dichromate / sulfuric acid system, Difficult to produce in large quantities; In addition, the waste liquid that produces after the reaction contains a large amount of chromium salts, and environmental pollution is bigger, is unfavorable for environmental protection, because the development of above-mentioned reason and the popularization of metsulfuron-methyl are hindered to a certain extent, to a certain extent impact on product development

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of dimethyl 2-nitroterephthalate

[0031] Put 926.97g of 98% sulfuric acid into a 1000ml four-neck bottle, stir to cool down to 10-15°C, slowly add 200.72g of 97% nitric acid dropwise; after adding, keep 10-15°C and add 300.0g of dimethyl terephthalate in batches After about 30 minutes of adding, control the reaction temperature at 15-20°C, keep warm for 30 minutes, and confirm the end point of the reaction with TLC. After the reaction was finished, the material was slowly diluted to 1854g of ice water, and a white solid was precipitated by stirring; after stirring for 15 minutes, it was suction filtered, and the filter cake was rinsed with 900ml of 5% sodium hydroxide aqueous solution, and then rinsed to neutrality with 500ml of water; the filter cake was put into Add 1500g of ethanol to a 3000ml four-necked bottle for recrystallization: first raise the temperature to 50-55°C to dissolve all the solids, then stir and cool down to below 5°C to separate o...

Embodiment 2

[0041] (1) Preparation of dimethyl 2-nitroterephthalate

[0042] Put 285g of 98% sulfuric acid into a 500ml four-necked bottle, stir to cool down to 10-15°C, slowly add 42g of 97% nitric acid dropwise; After the addition was completed in 30 minutes, the reaction temperature was controlled at 15-20°C, and after 30 minutes of heat preservation, the end point of the reaction was confirmed by TLC. After the reaction, the material was slowly diluted to 600g of ice water, and a white solid was precipitated by stirring; after stirring for 15 minutes, it was suction filtered, and the filter cake was rinsed with 300ml of 5% sodium hydroxide aqueous solution, and then rinsed to neutrality with 300ml of water; the filter cake was put into Add 600g of ethanol to a 1000ml four-neck bottle for recrystallization: first raise the temperature to 50-55°C to dissolve all the solids, then stir and cool down to below 5°C to allow the material to fully separate out; Vacuum drying at 60°C yielded 1...

Embodiment 3

[0052] (1) Preparation of dimethyl 2-nitroterephthalate

[0053] Put 430g of 98% sulfuric acid into a 500ml four-necked bottle, stir to cool down to 10-15°C, slowly add 73g of 97% nitric acid dropwise; After the addition was completed in 30 minutes, the reaction temperature was controlled at 15-20°C, and after 30 minutes of heat preservation, the end point of the reaction was confirmed by TLC. After the reaction, the material was slowly diluted to 650g of ice water, and a white solid was precipitated by stirring; after stirring for 15 minutes, it was suction filtered, and the filter cake was rinsed with 360ml of 5% sodium hydroxide aqueous solution, and then rinsed to neutrality with 300ml of water; the filter cake was put into Add 600g of ethanol to a 1000ml four-neck bottle for recrystallization: first raise the temperature to 50-55°C to dissolve all the solids, then stir and cool down to below 5°C to allow the material to fully separate out; Vacuum drying at 60°C yielded 1...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for preparing 2-amino-4-methanesulfonamide methylbenzoate. According to the method, dimethyl terephthalate serves as a raw material, and then 2-amino-4-methanesulfonamide methylbenzoate is prepared through nitrification, ammonolysis, dehydration, hydrogenation reduction and sulfonylation. The method has the advantages that the raw material is easy to obtain, the reaction conditions are mild, the yield is high, the byproducts are few, the pollution is little, and the like; the difficult problems in the existing mesosulfuron-methyl preparation processes that the raw material is expensive, the conditions are harsh, the pollution is serious, and the like are solved effectively.

Description

technical field [0001] The invention relates to a preparation method of an important intermediate of metsulfuron-methyl, in particular to a preparation method of 2-amino-4-methanesulfonamide methyl benzoate. Background technique [0002] The chemical name of Metsulfuron-methyl is 2-[3-(4,6-dimethoxypyrimidin-2-yl)ureasulfonyl]-4-methylsulfonamide methyl benzoate, which is German Bayer Crop Science Company The developed sulfonylurea herbicide works by inhibiting the acetolactate synthase, and the weed roots and leaves absorb the components and conduct them in the plant to stop the growth of the weeds, and then die. The drug efficacy test shows that this The drug has a good control effect on some broad-leaved weeds such as annual gramineous weeds of spring wheat and winter wheat and cow chickweed. The structural formula of sulfasulfuron-methyl is as follows: [0003] [0004] The method for preparing metsulfuron-methyl is mainly based on the Bayer patent now, and there are...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/06C07C303/38
Inventor 秦振伟刘琛施云龙陈国泉朱炯
Owner ZHEJIANG DINGLONG TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com