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A kind of azabicyclic complex catalyst and its preparation method and application

A technology of azabicyclic and complexes, which is applied in the field of azabicyclic tertiary amine complex catalysts and its preparation, and can solve problems such as environmental pollution, low yield, and uneconomical synthesis reaction process

Active Publication Date: 2022-06-10
内蒙古灵圣作物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Above prior art adopts azabicyclic tertiary amine compound as the catalyst of etherification reaction, conversion rate is about 92-95%, there is the problem of low yield, the crude product that obtains also needs to carry out recrystallization, just can obtain relatively High-purity products. In addition, azabicyclic tertiary amines have the characteristics of easy sublimation, forming organic volatiles and polluting the environment. In the later stage of the etherification reaction process, catalysts need to be supplemented. The price of catalysts is high, and the synthesis reaction process is uneconomical.

Method used

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  • A kind of azabicyclic complex catalyst and its preparation method and application
  • A kind of azabicyclic complex catalyst and its preparation method and application
  • A kind of azabicyclic complex catalyst and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1-6

[0076] Example 1-6 Preparation of azabicyclic tertiary amine complex catalyst

[0077] Examples 1-6 prepared the azabicyclic tertiary amine complex catalyst of the present invention by the method of the present application, the yields of the azabicyclic tertiary amine complexes were all above 85%, and Examples 1 and 3 used The mother liquor of the previous batch was used as the reaction solvent, and the yield reached more than 95%.

Embodiment 1

[0078] Example 1: Preparation of the complex of formula I-2 by using cuprous bromide and the previous batch of mother liquor

[0079] (1) Pretreatment of cuprous bromide

[0080] The cuprous bromide produced by industrial production or purchased by the reagent company has a trace amount of cupric bromide, and the color is light green. In order to ensure the catalytic effect, pretreatment is required.

[0081] Add 450g of 3% diluted HBr to the four-necked bottle, add 0.5g Na 2 SO 3 , remove the oxidized bromine or oxygen in dilute HBr, and at the same time reduce cupric ions to cuprous ions, quickly add 1000g of reagent grade CuBr, replace it with high-purity nitrogen three times, and stir at room temperature for about 2h, Since CuBr is insoluble in dilute HBr, CuBr 2 Dissolved in dilute HBr, in order to achieve the purpose of separation and purification, filter under nitrogen protection, rinse twice with absolute ethanol to remove water, and vacuum dry at 50-60 ° C for 2 ...

Embodiment 2

[0086] Example 2: Preparation of complexes of formula I-2 using cuprous bromide

[0087] (1) the pretreatment method of cuprous bromide is with embodiment 1

[0088] (2) Preparation of formula I-2

[0089] Measure 400 mL of anhydrous acetonitrile, start stirring, then add 287.48 g of cuprous bromide (99.7%) powder, under nitrogen protection, heat to 45-50° C. to dissolve, it is a light gray solution, ready for use.

[0090] In a four-necked flask, add 126.20g of 2-methyltriethylenediamine, add 200mL of acetonitrile, dissolve at room temperature, fill with nitrogen protection, and use a constant pressure addition funnel to drop the cuprous bromide solution prepared above into , the temperature is 20-30 ℃, after adding for about 20 minutes, light brown ligand compounds are continuously precipitated. After adding, stirring at room temperature for 1 hour, then cooling to -10 ℃, crystallization, nitrogen protection suction filtration, to avoid inhalation of water, and then use ...

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Abstract

The invention relates to an azabicyclic tertiary amine complex catalyst and a preparation method thereof. The azabicyclic tertiary amine complex catalyst can be used to synthesize 2-[2-[6-chloropyrimidin-4-yloxy]phenyl Methyl ]‑3,3‑dimethoxypropionate (III) and (E)‑2‑[2‑[6‑(2‑cyanophenoxy)pyrimidin‑4‑yloxy]phenyl] The preparation of ‑3‑methoxymethyl acrylate (Ⅴ) can significantly increase the yield of etherification reaction, and obtain a product with a purity greater than 99.4% and an appearance color of white powder.

Description

technical field [0001] The invention relates to an azabicyclic tertiary amine complex catalyst and a preparation method thereof. The azabicyclic tertiary amine complex catalyst can be used in the synthesis of (2-[2-[6-chloropyrimidin-4-yl] Oxy]phenyl]-3,3-dimethoxypropionic acid methyl ester (III) and (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy A special catalyst for methyl]phenyl]-3-methoxyacrylate (V). Background technique [0002] Methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate is an efficient and broad-spectrum agricultural sterilization It has multiple functions such as systemic absorption and conduction, prevention, protection and treatment, and has good control effects on plant powdery mildew, rust, glume blight, downy mildew and rice blast. At present, the industrial synthesis method with economic value is to use methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate and o-hydroxybenzonitrile Reaction preparation. Th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07F1/08C07D239/34C07D239/52
CPCB01J31/183C07F1/08C07D239/34C07D239/52B01J2531/16B01J2231/482B01J2231/40
Inventor 时叶强曹彤彤
Owner 内蒙古灵圣作物科技有限公司
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