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Preparation method of mepanipyrim

A technology of azoxystrobin and chloropyrimidine aniline, which is applied in the field of preparation of azoxystrobin fungicides, can solve the problems of severe equipment corrosion and low yield, and achieve the effects of low cost, high yield and mild reaction conditions

Inactive Publication Date: 2014-08-27
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the dehydration of acetic anhydride to prepare dehydroacetic acid needs to be carried out under the condition of high temperature (>200 °C) in the presence of a catalyst, and the final elimination reaction needs strong base high temperature catalysis, which seriously corrodes the equipment, and the yield of each step is not high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the preparation of N-(4-methyl-6-propynyl pyrimidin-2-yl) aniline

[0015] (1) Synthesis of benzoguanidine carbonate: Preparation of guanidine carbonate reference (patent number US5276186). Under stirring at room temperature, add 88.5 g (0.78 mol) of hydrochloric acid (32%) to 93.1 g of aniline (1.0 mol), until pH = 2, a large amount of heat is released and a large amount of precipitation is formed. This process needs to be completed within 30 min . Then, the mixture was heated to 85° C., and 92.4 g of an aqueous solution of cyanamide (50%) was added, and the process was completed within about 1 h. Then continue to add 22.1 g (0.19 mol) of hydrochloric acid (32%), so that the pH is in the range of 2.4 to 2.7. Keep stirring at 85°C for 2h, after the reaction mixture is cooled to 60°C, add 63.6g (0.6 mol) of sodium carbonate aqueous solution (170 mL of water) within 30min, the reaction solution is cooled to below 5°C, washed with water to obtain 148g of g...

Embodiment 2

[0019] Example two, the preparation of N-(4-methyl-6-oct-1-ynylpyrimidin-2-yl)aniline

[0020] (1) Synthesis of carbonate of benzoguanidine: same as Example 1;

[0021] (2) Synthesis of anilinopyrimidinone : With embodiment 1;

[0022] (3) Synthesis of 2-chloropyrimidinamine: same as Example 1;

[0023] (4) Synthesis of the target product azoxystrobin: Ar atmosphere, PdCl 2 (PPh 3 ) 2 (0.01 mmol, 10 mg, 0.1 mol%), CuI (0.5 mmol, 5 mol%) and 2-chloropyrimidinamine (10.0 mmol) in anhydrous oxygen-free dioxane (30 mL) solution was added dropwise octyne (15 mmol), after addition, add 10 mL Et 3 N, warm up to 100°C, stir for 12 h, cool to room temperature, add saturated NH 4 Cl (10 mL) quenched the reaction, extracted three times with ethyl acetate, and the organic phase was washed with saturated NaCl solution, NaSO 4Drying, the solvent is evaporated under reduced pressure, and the crude product is used sherwood oil: the eluent column chromatography of ethyl acetate=1:2...

Embodiment 3

[0024] Embodiment three, the preparation of N-(4-methyl-6-phenylethynylpyrimidin-2-yl) aniline

[0025] (1) Synthesis of carbonate of benzoguanidine: same as Example 1;

[0026] (2) Synthesis of anilinopyrimidinone : With embodiment 1;

[0027] (3) Synthesis of 2-chloropyrimidinamine: same as Example 1;

[0028] (4) Synthesis of the target product azoxystrobin: Ar atmosphere, PdCl 2 (PPh 3 ) 2 (0.01 mmol, 10 mg, 0.1 mol%), CuI (0.5 mmol, 5 mol%) and 2-chloropyrimidinamine (10.0 mmol) in anhydrous and oxygen-free dioxane (30 mL) were added dropwise (15 mmol), after addition, add 10 mL Et 3 N, warm up to 100°C, stir for 12 h, cool to room temperature, add saturated NH 4 Cl (10 mL) quenched the reaction, extracted three times with ethyl acetate, and the organic phase was washed with saturated NaCl solution, NaSO 4 Drying, the solvent is evaporated under reduced pressure, and the crude product is used sherwood oil: the eluent column chromatography of ethyl acetate=1:20...

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Abstract

The invention provides a preparation method of mepanipyrim and belongs to the field of pesticide chemical synthesis technologies. The preparation method of the mepanipyrim comprises the following steps: firstly, reacting phenyl guanidine salt with ethyl acetoacetate so as to prepare phenylamino pyrimidone, reacting the phenylamino pyrimidone with phosphorus oxychloride so as to prepare 2-chloro-pyrimidine phenylamine; subsequently, carrying out coupling and crossing reaction between the 2-chloro-pyrimidine phenylamine and alkyne so as to prepare mepanipyrim. The preparation method of mepanipyrim has the advantages that the used raw materials and reagents are cheap and easily available; the reaction process is simple, the reaction conditions are mild, the cost is low, the yield is high, a good condition is created for industrial large-scale production and commercialization of the products.

Description

technical field [0001] The invention belongs to the field of pesticides and relates to a preparation method of azoxystrobin fungicides. Background technique [0002] Azoxystrobin was synthesized for the first time by Lin Mao et al. from Japan Combination Chemical Company. In 1987, the Japan Plant Protection Association began the practical evaluation, and it was registered and listed in 1995. Azimethanil is an aniline steep fungicide with outstanding effects on botrytis cinerea, powdery mildew, apple scab, leaf spot, peach gray spot, scab and other diseases. The molecular formula of azoxystrobin is: C 14 h 13 N 3 , the molecular weight is: 223.27, and its chemical structure is as follows: [0003] . [0004] At present, there are two main methods for preparing azoxystrobin: (1) using formanilide and methanesulfonyl pyrimidine as raw materials, under the action of sodium cyanide or sodium hydroxide, azoxystrobin can be prepared in high yield, however The preparation pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42
CPCC07D239/42
Inventor 权正军燕中飞王喜存
Owner NORTHWEST NORMAL UNIVERSITY
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