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

2-(2-(5-acetamido-2, 4-dichlorophenyl) hydrazono) propionic acid compound and synthesis method thereof

A technology of dichlorophenyl and acetamido, applied to 2-(2-(5-acetamido-2, can solve problems such as narrow selection range, high cost of sulfentrazone, and instability under application conditions. , to achieve the effects of mild reaction conditions, high reaction yield, and cheap and easy-to-obtain raw materials

Pending Publication Date: 2022-02-11
浙大宁波理工学院
View PDF11 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned prior art all inevitably obtain the N-difluoromethyl substituted triazolinone ring—— This structure, then on the basis of the above structure, carry out subsequent reactions such as nitrification and reduction to obtain the final sulfentrazone; since the total yield of the two-step reaction is only about 70%, the sulfentrazone produced by this technical scheme High cost of amine
In addition, because the N-difluoromethyl substituted triazolinone ring is unstable under certain conditions (instability may occur under complex reaction conditions), it is limited by the stability of the group, making In the presence of N-difluoromethyl-substituted triazolinone ring, the method used for nitration and reduction on the benzene ring has a narrow selection range, which is not conducive to the continuous improvement of this technical solution

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
  • 2-(2-(5-acetamido-2, 4-dichlorophenyl) hydrazono) propionic acid compound and synthesis method thereof
  • 2-(2-(5-acetamido-2, 4-dichlorophenyl) hydrazono) propionic acid compound and synthesis method thereof
  • 2-(2-(5-acetamido-2, 4-dichlorophenyl) hydrazono) propionic acid compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 1. Add 64.80 g (0.40 mol) of 2,4-dichloroaniline and 300 ml of concentrated sulfuric acid to a 500 ml round-bottomed flask, and cool in an ice-water bath; add dropwise a mixture of 160 ml of concentrated sulfuric acid and 16 ml of concentrated nitric acid at 0°C, and dropwise add After completion, the reaction was continued at the same temperature for 2 hours. Then reaction mixture is added in 1500ml ice-water mixture, filter out precipitation, in Virahol / water mixed solvent (the volume ratio of the two in Virahol / water mixed solvent is 3:1, embodiment 2 is the same) 66.24 g (0.32 mol) of 2,4-dichloro-5-nitroaniline were obtained by crystallization in , with a yield of 80%.

[0042] 2. Add 200ml of dichloromethane, 62.10g (0.30mol) of 2,4-dichloro-5-nitroaniline and 66.79g (0.66mol) of triethylamine into a 500ml round bottom flask, and stir well. At room temperature, 86.35 g (0.33 mol) of acetyl chloride was added dropwise to the flask, and after the dropwise addition ...

Embodiment 2

[0055] 1. Add 81.00 g (0.50 mol) of 2,4-dichloroaniline and 330 ml of concentrated sulfuric acid into a 500 ml round bottom flask, and cool in an ice-water bath. A mixture consisting of 180ml of concentrated sulfuric acid and 18ml of concentrated nitric acid was added dropwise at 0°C, and the reaction was continued for 2 hours at the same temperature after the dropwise addition. The reaction mixture was added to 1600 ml of ice-water mixture, the precipitate was filtered off, and crystallized in isopropanol / water mixed solvent to obtain 80.73 g (0.39 mol) of 2,4-dichloro-5-nitroaniline, with a yield of 78%.

[0056] 2. Add 220 ml of chloroform, 62.10 g (0.30 mol) of 2,4-dichloro-5-nitroaniline and 54.51 g (0.69 mol) of pyridine into a 250 ml round bottom flask, and stir evenly at room temperature. At room temperature, 94.2 g (0.36 mol) of acetyl chloride was added dropwise to the flask, and after the dropwise addition was completed, the reaction was continued at room temperatur...

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 2-(2-(5-acetamido-2, 4-dichlorophenyl) hydrazono) propionic acid compound and a synthesis method thereof, and the method comprises the following steps: firstly introducing nitryl on a benzene ring in a first-step reaction which does not have a triazolinone ring structure; reducing into amino, wherein the triazolinone ring structure does not exist in the reaction of reducing to the amino group in the step; and at last, adopting a product for finally forming the sulfentrazone containing the triazolinone ring structure, wherein the problem of partial decomposition of the triazolinone ring can be avoided when the intermediate is used for synthesizing the sulfentrazone, so that byproducts are reduced, and the synthesis yield of the sulfentrazone is improved; the specific structural formula is shown in the specification.

Description

technical field [0001] The present invention relates to the technical field of synthesis of an important intermediate of sulfentrazone, in particular to an intermediate used in the preparation of sulfentrazone—2-(2-(5-acetylamino-2,4- Dichlorophenyl) hydrazino) propionic acid compound and its synthesis method. Background technique [0002] Sulfentrazone, its chemical structural formula is as follows: [0003] [0004] It is a herbicide of difluoromethyltriazolinone class, its chemical name is N-(2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3- Methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide, due to the good effect of this herbicide, there are many reports about its synthetic method, the most basic of which A synthetic method is as follows: [0005] [0006] (Zhang Yuanyuan, Sun Yonghui, Shi Yueping, Pesticides, 2013, 52 (4), 260-262.); The method is to use 2,4-dichloroaniline as raw material, through diazotization, hydrazone formation, ring formation, N ...

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): C07C249/16C07C251/76C07C209/76C07C211/52C07C231/12C07C233/43C07C231/02C07C233/15C07C241/02C07C243/22
CPCC07C209/76C07C231/12C07C231/02C07C241/02C07C249/16C07C211/52C07C233/43C07C233/15C07C243/22C07C251/76
Inventor 骆成才李玉麒
Owner 浙大宁波理工学院
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