Unlock instant, AI-driven research and patent intelligence for your innovation.

Synthesis method of metamifop

A technology of oxazolam and a synthesis method, applied in the field of organic synthesis, can solve the problems of low product purity, high cost, and many three wastes, etc., and achieve the effects of high purity, mild conditions and high yield

Active Publication Date: 2020-08-25
JIANGSU FUDING CHEM
View PDF3 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] To sum up, the existing synthetic methods of fenpyramid have their own disadvantages, such as high cost, many wastes, and low purity of the obtained product

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
  • Synthesis method of metamifop
  • Synthesis method of metamifop
  • Synthesis method of metamifop

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 333.7g (1mol) (R)-2-(4-((6-chlorobenzoxazole)oxy)phenoxypropionic acid (ee value: 99.6%) to a 2000mL four-neck flask under normal temperature and pressure 1000g dichloromethane, start stirring, add 162.1g (1mol) CDI in 5 batches within 30min, add 21.8g (0.1mol) ImTfOH, continue stirring at a temperature of 20°C for 1h.

[0032] Add 125.1g (1mol) N-methyl-o-fluoroaniline and 300g dichloromethane into a 2000mL four-necked flask, and drop (R)-2-(4-((6-chlorobenzoxazole) Oxygen) phenoxypropionic acid solution, control the dropping time at about 1 hour, control the temperature at 20°C during the dropping process, and stir and react at a temperature of 20°C for 2h after the dropping. After the reaction, the reaction solution is extracted with water 2 times, each time the water consumption was 200g, the organic phase was stripped of dichloromethane, and 422.4g of the oxafenamide product was obtained, the purity was 98.2%, the yield was 95.8%, and the ee value was 99.6%.

Embodiment 2

[0034] Add 333.7g (1mol) (R)-2-(4-((6-chlorobenzoxazole)oxy)phenoxypropionic acid (ee value: 99.6%) to a 2000mL four-neck flask under normal temperature and pressure 1000g acetonitrile, start stirring, add 162.1g (1mol) CDI in 5 batches within 30min, add 21.8g (0.1mol) ImTfOH, continue stirring at a temperature of 20°C for 1h.

[0035] Add 125.1g (1mol) of N-methyl-o-fluoroaniline and 300g of acetonitrile into a 2000mL four-necked flask, and drop (R)-2-(4-((6-chlorobenzoxazole)oxyl ) phenoxypropionic acid solution, control the dropping time at about 1 hour, control the temperature at 20°C during the dropping process, and stir and react at 20°C for 2h after the dropping is completed. After the reaction, extract 2 times from the reaction solution, 1000g of water and 1000g of dichloroethane were used for the first time, and the dichloroethane was removed from the organic phase to obtain 413.3g of the oxazifen product, with a purity of 96.3%, a yield of 93.7%, and an ee value of 9...

Embodiment 3

[0037] Add 333.7g (1mol) (R)-2-(4-((6-chlorobenzoxazole)oxy)phenoxypropionic acid (ee value: 99.6%) to a 2000mL four-neck flask under normal temperature and pressure 1000g dichloromethane, start stirring, add 162.1g (1mol) CDI in 5 batches within 30min, add 10.9g (0.05mol) ImTfOH, continue stirring at a temperature of 20°C for 1h.

[0038] Add 125.1g (1mol) N-methyl-o-fluoroaniline and 300g dichloromethane into a 2000mL four-necked flask, and drop (R)-2-(4-((6-chlorobenzoxazole) Oxygen) phenoxypropionic acid solution, control the dropping time at about 1 hour, control the temperature at 20°C during the dropping process, stir and react at 20°C for 2h after the dropping is completed. After the reaction, the reaction solution is extracted with water twice , the water consumption is 200g each time, and the dichloromethane is desorbed from the organic phase to obtain 418.6g of the oxapropen product, the purity is 97.6%, the yield is 94.9%, and the ee value is 99.6%.

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 synthesis method of metamifop, which comprises the step of carrying out substitution reaction on (R)-2-(4-((6-chlorobenzoxazole) oxy) phenoxy propionic acid and N-methyl o-fluoroaniline under the actions of a condensation reagent and a catalyst to obtain high-purity metamifop, wherein the condensation reagent is CDI, and ImTfOH is used as the catalyst. The synthesis method of metamifop is simple to operate, free of dangerous steps, safe and reliable; and a reaction system is nearly neutral, conditions are mild, and metamifop cannot be decomposed. According to the present invention, the production process of the raw material (R)-2-(4-((6-chlorobenzoxazole) oxy) phenoxy propionic acid is mature, the purity is high, the impurities cannot be introduced by the raw material, the prepared metamifop has characteristics of high purity and high yield, and the optical purity does not change along with the reaction system, such that large-scale industrial production can be achieved with the metamifop synthesis method.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a high-yield, high-purity synthesis method of fenpyramid. Background technique [0002] Metamifop, the chemical name is (R)-2-{(4-chloro-1,3-benzoxazol-2-yloxy)phenoxy}-2′-fluoro-N- Methylpropionanilide is an aryloxyphenoxypropionate herbicide developed by Korea Research Institute of Chemical Technology. It is safe and can control most of the main annual grass weeds, such as barnyardgrass, stephenia, crabgrass and goosegrass, and is mainly used for weeding in transplanted and direct seeded rice fields. Mefenpyramid has low toxicity, is environmentally safe, has wide compatibility, and is expected to be used for weeding other crops and lawns. It is a promising herbicide. [0003] At present, the synthesis technology of fenpyramid mainly includes: [0004] 1. The intermediate (R)-2-(4 -((6-chlorobenzoxazole)oxy)phenoxypropionyl chloride; under the action of an acid-binding agent,...

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): C07D263/58
CPCC07D263/58
Inventor 刘东卫张彦飞
Owner JIANGSU FUDING CHEM