Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of preparation method of ethyl 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoate

A technology of ethyl methylsulfonylbenzoate and dihydroisoxazole, which is applied to the preparation of ethyl 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoate field, can solve the problem of many steps, and achieve the effect of simple operation, good market prospect, and simple and easy post-processing

Active Publication Date: 2020-11-03
CHAMBROAD CHEM IND RES INST CO LTD
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above three routes for the synthesis of intermediate a have many steps, and a carbonyl insertion reaction is required in the later stage to obtain fenpyrazone

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

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of ethyl 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoate
  • A kind of preparation method of ethyl 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoate
  • A kind of preparation method of ethyl 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Synthesis of Compound A

[0040]

[0041] At room temperature, weigh 18.2g of Hagemann's ethyl ester, 12.98g of mercaptopropionic acid, 1.62g of p-toluenesulfonic acid, and 0.79g of pyridine into a 100ml round bottom flask, add 30ml of toluene, place the bottle in an oil bath, and heat up Reflux with water, react for 5 hours, the toluene phase is no longer turbid, and the reaction is complete; cool down to room temperature, add 30ml of water, stir and wash with water, remove excess mercaptopropionic acid, extract the water phase with 20ml of toluene again, combine the organic phase and then use 20ml After washing once with water, the organic phase was extracted, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain 23.33 g of compound A with a yield of 87.4%.

[0042] (2) Synthesis of compound B

[0043]

[0044] Add 3.35g of compound A, 5.1g of acetic anhydride and 1.21g of pyridinium p-toluenesulfonate into the rea...

Embodiment 2

[0058] (1) Compound A 2 Synthesis

[0059]

[0060] At room temperature, weigh 18.2g of Hagemann's ethyl ester, 13.2g of methyl mercaptopropionate, 1.62g of p-toluenesulfonic acid, and 0.79g of pyridine into a 100ml round bottom flask, add 30ml of toluene, and place the bottle in an oil bath , warmed up to reflux with water, reacted for 5 hours, the toluene phase was no longer turbid, and the reaction was completed; when it was lowered to room temperature, 30ml of water was added, stirred and washed with water to remove excess mercaptopropionic acid, and the aqueous phase was extracted once again with 20ml of toluene, and the organic phase was combined Wash once with 20ml of water, extract the organic phase, dry over anhydrous sodium sulfate, and remove the solvent by rotary evaporation to obtain 24.21g of compound A 2 , yield 85.2%.

[0061] (2) Synthesis of compound B

[0062]

[0063] Add compound A to the reaction vial 2 14.2g, 5.1g of acetic anhydride and 1.21g ...

Embodiment 3

[0077] (1) Synthesis of Compound A

[0078]

[0079] At room temperature, weigh 18.2g of Hagemann's ethyl ester, 12.98g of mercaptopropionic acid, 1.62g of p-toluenesulfonic acid, and 0.79g of pyridine into a 100ml round bottom flask, add 30ml of toluene, place the bottle in an oil bath, and heat up Reflux with water, react for 5 hours, the toluene phase is no longer turbid, and the reaction is complete; cool down to room temperature, add 30ml of water, stir and wash with water, remove excess mercaptopropionic acid, extract the water phase with 20ml of toluene again, combine the organic phase and then use 20ml After washing once with water, the organic phase was extracted, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain 23.33 g of compound A with a yield of 87.4%.

[0080] (2) Synthesis of compound B

[0081]

[0082] Add 3.35g of compound A, 5.1g of acetic anhydride and 1.21g of pyridinium p-toluenesulfonate into the rea...

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 provides a method of preparing a topramezone intermediate 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylphenyl ethyl formate with Hageman ethyl ester being an initial raw material. With Hageman ethyl ester being the raw material, a sulfhydrylation reaction is conducted with a sulfur-containing compound, an aromatization reaction is conducted under a catalyst, then a bond breakingring forming reaction is conducted under the effect of halohydrocarbon, an oximation reaction and an isoxazole ring forming reaction are conducted under an oximation catalyst, and then after a peroxidation reaction, the target product is obtained. The method has the advantages of being novel in route, and the monopoly of a traditional route is broken through; meanwhile, in the process route withHageman ethyl ester being the raw material, the reaction route is simple, safe and environmentally friendly, industrialization is easily achieved, and the method has a market prospect.

Description

technical field [0001] The invention relates to a preparation method of a new merazenone intermediate 2-methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoic acid ethyl ester. Background technique [0002] Fenpyrazone is a new type of herbicide developed by BASF in Germany. This herbicide has significant effects on weeds resistant to glyphosate, triazines, acetolactate synthase inhibitors and acetyl-CoA carboxylase inhibitors. It is a broad-spectrum post-emergence herbicide and can effectively control annual grasses and broad-leaved weeds in corn fields. [0003] 2-Methyl-3-[4,5-dihydroisoxazole]-4-methylsulfonylbenzoic acid ethyl ester is the most important intermediate in the synthesis of fenpyrazole, while the currently reported synthetic benzopyrazole The oxalone intermediate is mainly 3-[3-bromo-2-methyl-6-(methylsulfonyl)phenyl]-4,5-dihydroisoxazole (a), and its synthetic route mainly includes the following three kind: [0004] (1) With 2-methyl-3-aminobenzoic aci...

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 Patents(China)
IPC IPC(8): C07D261/04
CPCC07D261/04
Inventor 冯其龙马韵升陈梅梅刘克锋樊其艳张蒙黄文昌
Owner CHAMBROAD CHEM IND RES INST CO LTD
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com