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

Process for preparation of azoxystrobin and intermediates thereof

A technology of azoxystrobin and methyl propionate, applied in the field of preparing strobilurin compounds, capable of solving the problems of low purity and low yield

Pending Publication Date: 2021-12-07
UNITED PHOSPHORUS LTD
View PDF10 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Prior Art Processes for the Preparation of Azoxystrobin Provide Intermediates and Final Compounds in Low Yields and Purities

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
  • Process for preparation of azoxystrobin and intermediates thereof
  • Process for preparation of azoxystrobin and intermediates thereof
  • Process for preparation of azoxystrobin and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0239] (E) Preparation of methyl 2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (compound IIa)

[0240] To a stirred mixture of 3-(methoxymethylene)-2(3H)-benzofuranone (97%, 91 g, 0.5 mol) in methyl formate (275 g) was added 4, 6-Dichloropyrimidine (98%, 92 g, 0.605 mol). At 10°C to 15°C, 1,8-diazabicyclo[5,4.0]undec-7-ene (0.038g, 0.249mmol, 0.05mol%) was added to the above reaction mixture, then dropwise Add sodium methoxide (30%, 110 g, 0.61 mol) in methanol. After the addition was complete, the reaction mass was maintained at 10°C to 15°C for 1 hour. Methyl formate was then distilled off from the mixture while maintaining the temperature below 55°C. Toluene (300ml) and water (200ml) were added to the remaining residue, and the mixture was stirred at 60°C to 65°C. The mixture was cooled to room temperature, and the organic layer was separated. Toluene was distilled off under reduced pressure, and the oily residue was heated to 130°C to 135°C. Potassium b...

Embodiment 2

[0242] (E) Preparation of methyl 2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (compound IIa)

[0243] To a stirred mixture of 3-(methoxymethylene)-2(3H)-benzofuranone (97%, 91 g, 0.5 mol) in methyl formate (275 g) was added 4, 6-Dichloropyrimidine (98%, 92 g, 0.605 mol). At 10°C to 15°C, 1,5-diazabicyclo[4.3.0]non-5-ene (0.031 g, 0.249 mmol, 0.05 mol%) was added to the reaction mixture followed by dropwise addition of sodium methoxide (30% in methanol, 110 g, 0.61 mol). The reaction mass was maintained at 10°C to 15°C for 1 hour. The methyl formate was then distilled off while keeping the temperature below 55°C. Toluene (300ml) and water (200ml) were added to the residue, and the mixture was stirred at 60°C to 65°C. The mixture was cooled to room temperature, and the organic layer was separated. Toluene was distilled off under reduced pressure, and the oily residue was heated to 130°C to 135°C. Potassium bisulfate (1.36 g, 0.01 mol) was added and the reactio...

Embodiment 3

[0244] Embodiment 3 (comparative example)

[0245] Preparation of (E)-methyl 2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (IIa) in the absence of catalyst:

[0246] To a stirred mixture of 3-(methoxymethylene)-2(3H)-benzofuranone (97%, 91 g, 0.5 mol) in methyl formate (275 g) was added 4, 6-Dichloropyrimidine (98%, 92 g, 0.605 mol). Sodium methoxide (30% in methanol, 110 g, 0.61 mol) was added dropwise to the reaction mixture at 10°C to 15°C. The reaction mass was maintained at 10°C to 15°C for 1 hour. Methyl formate was distilled off at atmospheric pressure while maintaining the temperature below 55°C. Toluene (300ml) and water (200ml) were added to the residue, and the mixture was heated to 60°C to 65°C. The mixture was cooled to room temperature, and the organic layer was separated. Toluene was distilled off under reduced pressure, and the oily residue was heated to 130°C to 135°C. Potassium hydrogen sulfate (1.36 g, 0.01 mol) was added to the mixture, ...

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 present invention relates to a process for preparation of strobilurin compound, azoxystrobin and its intermediates using a catalyst selected from 1,8-Diazabicyclo[5.4.0]undec-7-ene or 1,5-Diazabicyclo[4.3.0]non-5-ene, salts thereof, or derivatives thereof.

Description

technical field [0001] The present invention relates to a method for preparing strobilurin compounds. More specifically, the present invention relates to a method for preparing azoxystrobin and a method for preparing intermediate compounds useful for the preparation of azoxystrobin. Background technique [0002] Strubilurins are broad-spectrum fungicides and are widely used insecticides in foliar applications and seed treatments. Owing to their broad-spectrum activity profile, strobilurins are an important class of fungicides. Notable among this class of compounds are azoxystrobin, trifloxystrobin, fluoxastrobin and picoxystrobin. [0003] EP 382375 discloses various derivatives of acrylic acid, including azoxystrobin, useful as fungicides. The patent also discloses a method for preparing azoxystrobin and its intermediates. [0004] WO2008043978 discloses a method for preparing azoxystrobin using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalyst. [0005] WO2017060917...

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): C07D239/52C07D487/04
CPCC07D239/52C07D487/04
Inventor 普拉尚·瓦桑特·基尼桑托什·甘帕特·谢尔克
Owner UNITED PHOSPHORUS LTD
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