Preparation method of pydiflumetofen

The technology of fluconazole and p-chloroaniline, which is applied in the field of preparation of original drug compounds, can solve the problems of low reaction yield, high preparation cost, difficult synthesis route and the like, and achieve the effect of reducing cost

Active Publication Date: 2018-10-02
WUHAN INSTITUTE OF TECHNOLOGY
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0007] In order to solve the technical defects that the synthesis route of flufenapyramide in the prior art is difficult to be industrialized, and the preparation cost is high and the reaction yield is low, the present invention proposes a method for preparing flufenapyroxylamide, which comprises the following steps:

Method used

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  • Preparation method of pydiflumetofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038](1) Synthesis of 4´-chloropropiophenone

[0039]

[0040] Cool the mixture of 40.0g (0.4mol) isopropenyl acetate, 51.0g (0.4mol) p-chloroaniline, 58.0g (0.42mol) potassium carbonate and 200mL acetone to 0~5°C, add dropwise 31.5g (0.42mol) ethyl Base nitrite, dropwise time 30min, then rise to room temperature, continue to stir for 3h. Remove the solvent acetone, add 200mL of water, adjust the pH value to 10-11 with 10% sodium hydroxide solution, a solid precipitates, filter, wash the filter cake with water, and then recrystallize with methanol to obtain 54.05g of yellow solid . Yield 80.2%.

[0041] (2) Synthesis of 2´, 4´, 6´-trichloropropiophenone

[0042]

[0043] In a 250mL four-necked reaction flask equipped with a stirrer, a thermometer, and a condenser tube, add 67.4g (0.4mol) 1-(4-chlorophenyl) acetone-2, 1.6g (0.01mol) ferric chloride and 100ml of carbon tetrachloride. Heat to 50~60°C and react for 2h. 35 g (0.5 mol) of chlorine gas was introduced, an...

Embodiment 2

[0059] (1) Synthesis of 4´-chloropropiophenone

[0060] Cool the mixture of 10.0g (0.1mol) of isopropenyl acetate, 12.7g (0.1mol) of p-chloroaniline, 16.5g (0.12mol) of potassium carbonate and 100mL of acetone to 0~5°C, and dropwise add 12.40g (0.12mol) of t- Butyl nitrite was added dropwise for 40 minutes, then rose to room temperature and continued to stir for 6 hours. The solvent acetone was removed, 100mL of water was added, and the pH value was adjusted to 10-11 with 10% sodium hydroxide solution. Solids were precipitated, filtered, the filter cake was washed with water, and then recrystallized with methanol to obtain 12.6g of yellow solids. . Yield 75.2%.

[0061] (2) Synthesis of 2´, 4´, 6´-trichloropropiophenone

[0062] Add 16.8g (0.1mol) of 1-(4-chlorophenyl)acetone-2 and 100ml of carbon tetrachloride into a 250mL four-necked reaction flask equipped with a stirrer, a thermometer, and a condenser. Heat to 50~60°C, add 29.4g (0.22mol) N-chlorosuccinimide in batches...

Embodiment 3

[0074] The nitrite in Example 3 is ethyl nitrite; the molar ratio of p-chloroaniline, isopropenyl acetate and nitrite is 1:1.0:1.0; 4´-chloropropiophenone described in step (2) The molar ratio with chlorine gas is 1:2; the carbonyl reduction reaction between 2´,4´,6´-trichloropropiophenone and sodium borohydride described in step (3) is 1:1; the step ( 4) The molar ratio of 1-(2´,4´,6´-trichlorophenyl)-2-propanol to thionyl chloride is 1:1. Fu acid agent is triethylamine. Other operations are similar to Embodiment 1.

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Abstract

The invention provides a preparation method of pydiflumetofen, and belongs to the field of preparation of technical compounds. The preparation method of pydiflumetofen comprises the following steps: (1) performing a reaction on p-chloroaniline and isopropenyl acetate to obtain 4'-chloropropiophenone; (2) performing benzene ring chlorination to obtain 2',4',6'-trichloropropiophenone; (3) performinga carbonyl reduction reaction to obtain 1-(2',4',6'-trichlorophenyl)-2-propanol; (4) performing hydroxyl halogenation to obtain 1-(2',4',6-trichlorophenyl)-2-chloropropane; (5) performing amination on 1-(2,4,6-trichlorophenyl)-2-chloropropane and O-methylhydroxylamine to obtain O-methyl N-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-hydroxylamine; (6) performing a substitution reaction on the product obtained in step (5) and 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride under the action of an acid binding agent to obtain pydiflumetofen. By improving the preparation process of pydiflumetofen and changing a synthetic route of an intermediate, a traditional reduction process of sodium cyanoborohydride for oxime is omitted, and production cost is reduced.

Description

technical field [0001] The invention belongs to the field of preparation of original drug compounds, and in particular relates to a preparation method of flufenapyramide. Background technique [0002] Pydiflumetofen chemical name: 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(RS)-1-methyl-2-(2,4, 6-trichlorophenyl)ethyl]pyrazole-4-carboxamide. The chemical structural formula is: [0003] [0004] Pydiflumetofen is the latest pyrazole amide fungicide developed by Syngenta. Pydiflumetofen has a broad spectrum, high efficiency and is suitable for many crops. Fluxapylaxon has the highest activity against leaf spot and powdery mildew, which are the most common diseases in agricultural production. Fluxapylaxon is effective against difficult-to-control diseases such as Botrytis Diseases caused by pathogenic bacteria such as Sclerotinias pp. and Corynesporas pp. are highly effective. The occurrence of these diseases will cause serious losses in crop yields such as grapes, peanuts ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14
CPCC07D231/14
Inventor 刘安昌黄时祥汪焱鲁包洋郑怡倩
Owner WUHAN INSTITUTE OF TECHNOLOGY
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