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

Method for preparing mesosulfuron-methyl by one-pot method

A technology for preparing methyldisulfuron-methyl and methoxycarbonylbenzenesulfonamide, which is applied in the field of one-pot preparation of methyldisulfuron-methyl, can solve the problems of low product purity and yield, difficult separation, increased operation difficulty, labor intensity of workers, etc. The problem is to achieve the effect of high product purity and yield, and easy operation.

Pending Publication Date: 2022-02-01
江苏省农用激素工程技术研究中心有限公司 +1
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the applicant found that: 5-methylsulfonylaminomethyl-2-methoxycarbonylbenzenesulfonamide has poor solubility in acidic and neutral systems, so the above-mentioned acid washing and washing will lead to 5-methylsulfonyl Aminomethyl-2-methoxycarbonylbenzenesulfonamide is separated out from the reaction system, which will not only cause the viscosity of the system to be relatively large, thereby making it difficult to separate, thereby increasing the difficulty of operation and the labor intensity of the workers, and will also lead to uneven product purity and yield. lower

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）

[0024] The one-pot method of the present embodiment prepares the method for methylsulfuron-methyl specifically as follows:

[0025] Add 24.4g (0.1mol) 5-aminomethyl-2-methoxycarbonylbenzenesulfonamide, 45.6g (0.3mol) DBU and 122g acetonitrile into a 500mL reaction flask, control the temperature at 5±1°C, and add 12g ( 0.105mol) of methanesulfonyl chloride, continue to control the temperature at 5±1°C for the first step of mesylation reaction for 3h after dropping.

[0026] After passing the central control, directly add 30.3g (0.11mol) of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine into the reaction flask, and stir at ambient temperature for the second condensation reaction for 2h.

[0027] After the reaction is over, acetonitrile is recovered by distillation under reduced pressure, then lowered to ambient temperature, 200g of water is quickly added dropwise to the reaction flask, stirred for 0.5h, and the pH is adjusted to 4.5 with hydrochloric acid, suction filtered after...

Embodiment 2～ Embodiment 7）

[0029] The one-pot method for preparing methylsulfuron-methyl in each embodiment is basically the same as that in Example 1, and the differences are shown in Table 1.

[0030] Table 1

[0031] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 5-Aminomethyl-2-methoxycarbonylbenzenesulfonamide 24.4g (0.1mol) 24.4g (0.1mol) 24.4g (0.1mol) 24.4g (0.1mol) 24.4g (0.1mol) 24.4g (0.1mol) 24.4g (0.1mol) Methanesulfonyl chloride 12g (0.105mol) 13.7g (0.12mol) 11.5g (0.1mol) 12g (0.105mol) 12g (0.105mol) 12g (0.105mol) 12g (0.105mol) 4,6-Dimethoxy-2-phenoxycarbonylaminopyrimidine 30.3g (0.11mol) 30.3g (0.11mol) 30.3g (0.11mol) 41.3g (0.15mol) 27.5g (0.1mol) 30.3g (0.11mol) 30.3g (0.11mol) DBU 45.6g (0.3mol) 45.6g (0.3mol) 45.6g (0.3mol) 45.6g (0.3mol) 45.6g (0.3mol) 60.8g (0.4mol) 30.4g (0.2mol) Methsulfuron-methyl 45.2g 45.1g 44.1g 45.3g 43.7g 45.0g 43.0g ...

Embodiment 8）

[0033] The one-pot method of the present embodiment prepares the method for methylsulfuron-methyl specifically as follows:

[0034] Add 122g (0.5mol) 5-aminomethyl-2-methoxycarbonylbenzenesulfonamide, 228g (1.5mol) DBU and 610g acetonitrile into a 2L reaction flask, control the temperature at 5±1°C, add 60g (0.525mol) ) methanesulfonyl chloride, continue to control the temperature at 5±1°C for the first step of mesylation reaction for 3h after dropping.

[0035] After passing the central control, directly add 151.3g (0.55mol) 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine into the reaction flask, and stir at ambient temperature for the second condensation reaction for 2h.

[0036] After the reaction is over, acetonitrile is recovered by distillation under reduced pressure, then lowered to ambient temperature, 1000g of water is quickly added dropwise to the reaction flask, stirred for 0.5h, and the pH is adjusted to 4.5 with hydrochloric acid, suction filtered after stirring fo...

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 discloses a method for preparing mesosulfuron-methyl by a one-pot method, which comprises the following steps: carrying out first-step methylsulfonylation reaction on 5-aminomethyl-2-methoxycarbonyl benzene sulfonamide and methylsulfonyl chloride in an organic solvent in the presence of 1, 8-diazabicyclo undec-7-ene; and directly adding 4, 6-dimethoxy-2-phenoxy carbonyl aminopyrimidine into an untreated system after the first-step methylsulfonylation reaction, and carrying out a second-step condensation reaction. According to the method, DBU and acetonitrile are respectively adopted as an acid-binding agent and a solvent in methylsulfonylation and are carried out at a relatively low temperature, so that an intermediate does not need to be separated by acid washing and water washing after methylsulfonylation, instead, the 4,6-dimethoxy-2-phenoxy carbonyl aminopyrimidine is directly added to prepare mesosulfuron-methyl; therefore, the separation of the 5-methylsulfonylamino methyl-2-methoxycarbonyl benzene sulfonamide is avoided, the operation is simple and convenient, and the purity and the yield of the product are relatively high.

Description

technical field [0001] The invention belongs to the technical field of herbicide preparation, and in particular relates to a one-pot method for preparing methylsulfuron-methyl. Background technique [0002] The chemical name of Mesosulfuron-methyl is 2-[3-(4,6-dimethoxypyrimidin-2-yl)ureasulfonyl]-4-methanesulfonamidomethylbenzoate . It is a new type of sulfonylurea herbicide developed by Bayer Company of Germany in 2002. Regarding sulfonylurea herbicides, it is the largest class of herbicides in the world. It mainly works by inhibiting acetolactate synthase, miscellaneous Grass roots and leaves absorb it, conduct it in the plant body, and stop the growth of weeds to achieve the effect of weeding. The herbicide has a good control effect on winter wheat, spring wheat annual grass weeds and some broad-leaved weeds such as chickweed, and the demand in my country's herbicide market is showing an upward trend. [0003] At present, methylsulfuron methyl is mainly composed of 5-...

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
IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor 蒋旭明邹佩佩刘晓佳杨传鹏刘超孙永辉
Owner 江苏省农用激素工程技术研究中心有限公司
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