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Catalyst system and method for preparation of azoxystrobin or intermediates thereof with the same

A technology of azoxystrobin and intermediates, applied in the field of catalyst systems prepared by azoxystrobin and its intermediates, can solve the problems of difficult control of reaction conditions and low yield, and achieve short reaction time, high yield and conversion rate high effect

Active Publication Date: 2019-03-29
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN103265496A and CN103467387A pointed out that using 1,4-diazabicyclo[2.2.2]octane as a catalyst to prepare azoxystrobin and its intermediates, the reaction conditions are not easy to control, and the yield is not high. The preparation method of azoxystrobin and its intermediates catalyzed by the azabicyclic tertiary amine compound of the structure, under the catalytic system, the preparation yield and product content of azoxystrobin are improved

Method used

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  • Catalyst system and method for preparation of azoxystrobin or intermediates thereof with the same
  • Catalyst system and method for preparation of azoxystrobin or intermediates thereof with the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1 This example is used to illustrate the preparation of azoxystrobin shown in formula 1

[0067] Add dry toluene (100mL), salicylonitrile (0.105mol, 12.50g), compound E-2-{2-[6-chloropyrimidin-4-yloxy]benzene Base}-3-methoxymethyl acrylate (0.1mol, 32.07g), potassium carbonate (0.08mol, 11.06g) and catalyst 2-carbonyl-1,4-diazabicyclo[2.2.1]heptane ( 0.01mol , 1.14g), start stirring, heat to 85°C, keep warm for 4h, HPLC detects that the content of salicylonitrile is less than 0.5%, cool the reaction system to 40~50°C, add 20mL of water, let stand to separate after stirring, separate The water phase and the toluene phase were washed once with 10 mL of water, the water phase was separated again, the toluene phase was evaporated to dryness, and recrystallized to obtain azoxystrobin shown in formula 1, with a content of 98.6% and a yield of 97.9%.

Embodiment 2

[0069] This embodiment is used to illustrate the impact of catalyst dosage on the reaction in the preparation process of azoxystrobin shown in formula 1

[0070] Add dry toluene (100mL), salicylonitrile (0.105mol, 12.50g), compound E-2-{2-[6-chloropyrimidin-4-yloxy]benzene Base}-3-methoxymethyl acrylate (0.1mol, 32.07g), potassium carbonate (0.08mol, 11.06g) and catalyst 2-carbonyl-1,4-diazabicyclo[2.2.1]heptane ( 0.001mol , 0.114g), start stirring, heat to 85°C, keep warm for 4h, HPLC detects that the content of salicylonitrile is less than 0.5%, cool the reaction system to 40~50°C, add 20mL of water, leave to separate after stirring, separate The water phase and the toluene phase were washed once with 10 mL of water, the water phase was separated again, the toluene phase was evaporated to dryness, and recrystallized to obtain azoxystrobin shown in formula 1, with a content of 98.6% and a yield of 97.6%.

Embodiment 3

[0072] Add dry toluene (100mL), salicylonitrile (0.105mol, 12.50g), compound E-2-{2-[6-chloropyrimidin-4-yloxy]benzene Base}-3-methoxymethyl acrylate (0.1mol, 32.07g), potassium carbonate (0.08mol, 11.06g) and catalyst 2-carbonyl-1,4-diazabicyclo[2.2.1]heptane ( 0.0005mol , 0.057g), start stirring, heat to 85°C, keep warm for 8h, HPLC detects that the content of salicylonitrile is less than 0.5%, cool the reaction system to 40~50°C, add 20mL of water, let it stand for stratification after stirring, separate The water phase and the toluene phase were washed once with 10 mL of water, the water phase was separated again, the toluene phase was evaporated to dryness, and recrystallized to obtain azoxystrobin shown in formula 1, with a content of 98.3% and a yield of 97.3%.

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Abstract

The invention relates to a catalyst system, which comprises one or more of a methano-containing azabicyclo compound or salt thereof, an aza cage compound or salt thereof. The invention also relates toa method for preparation of azoxystrobin or intermediates thereof with the catalyst system. The efficient catalytic system utilized by the invention and the method for preparation of azoxystrobin orintermediates thereof have the characteristics of easily controllable process, short reaction time, high conversion rate, low energy consumption, etc., and are suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of chemical industry and relates to the preparation of a fungicide, in particular to a catalyst system prepared from azoxystrobin and its intermediate. Background technique [0002] Azoxystrobin is a new type of high-efficiency, broad-spectrum, systemic methoxyacrylate fungicide, the chemical name is (E)-2-[2-[6-(2-cyanophenoxy)pyrimidine- 4-yloxy]phenyl]-3-methyl methoxyacrylate, the structural formula is shown in formula 1. The fungicide can be used for stem and leaf spray, seed treatment, and soil treatment, and has good activity against almost all fungal diseases. It has no cross-resistance with existing fungicides and is widely used in grains, rice, grapes, potatoes, fruit trees and other crops. Azoxystrobin is a fungicide used in a large amount in the world. A large number of patent documents disclose its synthesis method. At present, the main synthesis route of azoxystrobin is as follows: [0003] . [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D239/52C07D239/34C07D213/643
CPCC07D213/643C07D239/34C07D239/52B01J31/0241B01J31/0244B01J31/0271
Inventor 范朝辉王利超赵娜张耀林李立华高倩贾成国
Owner HEBEI VEYONG BIO CHEM
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