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

A kind of preparation method of isoxaflutole key intermediate

A technology of isoxaflutole and intermediates, applied in the field of pesticide chemistry, can solve problems such as difficult control and impact on industrialization, achieve mild reaction, increase yield and purity, and reduce production costs

Active Publication Date: 2022-06-24
JIANGSU FLAG CHEM IND
View PDF12 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Publication No. CN1125940A discloses the reaction of 2-(methylthio)-4-(trifluoromethyl)benzonitrile and cyclopropyl methyl ketone, but in the process of preparing amino vinyl ketone, pyrimidine and amide The impurities are all above 4%, which is difficult to control, and the yield is only 91% or lower, which seriously affects industrialization

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 isoxaflutole key intermediate
  • A kind of preparation method of isoxaflutole key intermediate
  • A kind of preparation method of isoxaflutole key intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of Intermediate I:

[0030]

[0031] Step (1): Preparation of intermediate I, under nitrogen protection, 70.27g (0.3mol) 1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone was mixed with 21.13g (0.315mol) cyclopropanecarbonitrile was dissolved in 182.8g of 2-methyl-tetrahydrofuran, 31.71g (0.33mol) of sodium tert-butoxide was added, the temperature of the mixture was raised to 40°C for 3 hours, the temperature was lowered to room temperature, and 60.26g was added. (0.33mol) 20% hydrochloric acid aqueous solution was adjusted to neutral pH to stop the reaction, the aqueous phase was separated, and the organic phase was concentrated to obtain 3-amino-3-cyclopropyl-1-(2-(methylthio) as a yellow liquid) -4-(trifluoromethyl)phenyl)-2-ene-1-propanone is dissolved in 2-methyl-tetrahydrofuran, namely intermediate I, qualitative content 99%, weight yield 99%, 1 H NMR (400MHz, DMSO): δ10.06(s, 1H), 7.92(s, 1H), 7.60(d, J=7.8Hz, 1H), 7.51-7.43(m, 2H), 5.15(d, J ...

Embodiment 2

[0034] Step (1): Preparation of Intermediate I, under nitrogen protection, 281.09g (1.2mol) 1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone was mixed with 82.12g (1.224mol) cyclopropanecarbonitrile was dissolved in 618g 2-methyl-tetrahydrofuran, 126.85g (1.32mol) sodium tert-butoxide was added, the temperature of the mixture was increased to 45°C for 2.5 hours, the temperature was lowered to room temperature, 240.9g ( 1.32mol) 20% hydrochloric acid aqueous solution adjusts pH value to neutrality to stop the reaction, separates the water phase, and the organic phase is used for feeding step (2), and the qualitative content is 99%;

[0035] Step (2): Preparation of 1-cyclopropyl-3-(2-(methylthio)-4-(trifluoromethyl)phenyl)propyl-1,3-dione, in step (1) In the organic phase, add 175.2 g (1.44 mol) of 30% aqueous hydrochloric acid solution, raise the temperature to 50° C. for 3 hours, separate the aqueous phase, and concentrate the organic phase to obtain a pale yellow solid 1...

Embodiment 3

[0037]Step (1): Preparation of intermediate I, under nitrogen protection, 140.54g (0.6mol) 1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone was mixed with 44.28g (0.66mol) cyclopropanecarbonitrile was dissolved in 562.16g of 2-methyl-tetrahydrofuran, 74.96g (0.78mol) of sodium tert-butoxide was added, the temperature of the mixture was raised to 50°C for 3 hours, the temperature was lowered to room temperature, and 109.5g was added. (0.6mol) 20% hydrochloric acid aqueous solution adjusts the pH value to neutrality and stops the reaction, separates the aqueous phase, and concentrates the organic phase to obtain the intermediate I of the yellow liquid, the qualitative content is 98%, and the weight yield is 98%;

[0038] Step (2): Preparation of 1-cyclopropyl-3-(2-(methylthio)-4-(trifluoromethyl)phenyl)propyl-1,3-dione, 176.64 g (0.576 g) mol) Intermediate I was dissolved in 2-methyl-tetrahydrofuran, 91.13g (0.749mol) of 30% aqueous hydrochloric acid was added, the temperatu...

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 the field of pesticide chemistry, in particular to a method for preparing a key intermediate of isoxaflutole, comprising the following steps: under the protection of an inert gas, 1-(2-(methylthio)-4-(trifluoro Methyl)phenyl)ethanone and cyclopropanecarbonitrile are dissolved in an organic solvent, and a strong base is added to heat-treat the mixture. After the reaction is completed, an acidifying solution is added to adjust the pH value to neutral, the water phase is separated, and the organic phase is concentrated, that is Obtain intermediate I; Dissolve intermediate I in an organic solvent, add water and strong acid, heat treatment reaction, separate the aqueous phase after the completion of the reaction, concentrate the organic phase to obtain 1-cyclopropyl-3-(2-(methylthio )‑4‑(trifluoromethyl)phenyl)propyl‑1,3‑dione. The preparation method of the isoxaflutole key intermediate provided by the invention has mild reaction, less impurities and solid waste generation, improves the yield and purity of the product, reduces production cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of pesticide chemistry, in particular to isoxaflutole key intermediate 1-cyclopropyl-3-(2-(methylthio)-4-(trifluoromethyl)phenyl)propyl-1, The preparation method of 3-diketone. Background technique [0002] Isoxaflutole is an isoxazole herbicide discovered by Rhone-Planck (now Bayer) in 1992. It has good systemic activity and is absorbed through the rhizomes and foliage of crops. , conducted throughout the plant in the phloem and xylem. Listed in Jamaica in 1996, it is used to control broad-leaved weeds and grass weeds in corn and sugarcane fields, and can control more than 50 types of grass weeds (such as crabgrass, oxtenoid, foxtail, sagebrush, etc.) and broad-leaved weeds. Weeds (Abalone, Xanthium, Amaranth, Quinoa, Polygonum serrata, Kochia, mustard, purslane, chickweed, nightshade, mother-in-law, etc.). Currently registered in more than 30 countries. [0003] 1-Cyclopropyl-3-(2-(methylthio)-4-(trifluoromethyl...

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): C07C319/20C07C323/22C07C323/32
CPCC07C319/20C07C323/32C07C2601/02C07C323/22
Inventor 赵渭张璞吴耀军黄瑞琦王正旭侯远昌
Owner JIANGSU FLAG CHEM IND