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Epoxiconazole intermediate, preparation method thereof, and preparation method of epoxiconazole

A technology of epoxiconazole and intermediates, which is applied in the field of preparation of epoxiconazole intermediates and epoxiconazole, can solve the problems of high environmental protection, three wastes, unstable and dangerous reaction reagents, etc., and achieve less pollution of three wastes and safety High performance and simple steps

Active Publication Date: 2019-02-01
JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Existing methods often require the use of phosphine reagents, Grignard reagents, peroxides, and reducing agents. There are many three wastes, unstable reaction reagents, and high hazards, which do not meet the requirements of green environmental protection and are not conducive to industrial production.

Method used

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  • Epoxiconazole intermediate, preparation method thereof, and preparation method of epoxiconazole
  • Epoxiconazole intermediate, preparation method thereof, and preparation method of epoxiconazole
  • Epoxiconazole intermediate, preparation method thereof, and preparation method of epoxiconazole

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Embodiment 1

[0067] The preparation method of epoxiconazole of this embodiment has the following steps:

[0068] (1) Add Br dropwise to the HOAc (180mL) solution of the compound of formula I (0.4mol, 100g) at 0°C 2 (0.4mol, 63.2g) in HOAc (20mL) solution. After the addition was completed, the reaction was carried out at room temperature for 2 hours. The reaction solution was concentrated and diluted with ethyl acetate solvent, and then washed with 10% sodium sulfite solution and saturated sodium bicarbonate solution respectively, and the organic phase was dried with anhydrous sodium sulfate and concentrated to obtain the compound of formula II (X=Br, 132g) , Orange solid, content 98%, yield 99%.

[0069] (2) At 0°C, to a solution of trimethylsulfoxide bromide (0.4mol, 68.8g) in DMSO (dimethylsulfoxide) (800mL), add NaH (60%, 16.0g, 0.4 mol), the reaction solution was stirred at room temperature for 30 minutes. The temperature was lowered to 0°C, and a DMSO (200 mL) solution of the compound o...

Embodiment 2

[0073] The preparation method of epoxiconazole of this embodiment has the following steps:

[0074] (1) At 0°C, add dropwise an acetic acid solution (2.0 mL) with a mass percentage of 30% HBr and Br to the chloroform (900 mL) solution of the compound of formula I (0.4 mol, 100 g) 2 (0.4mol, 63.2g) in chloroform (80mL) solution. After the addition was completed, the reaction was carried out at 60°C for 4 hours. The reaction solution was washed successively with 10% sodium sulfite solution and saturated sodium bicarbonate solution, and the organic phase was dried with anhydrous sodium sulfate and concentrated to obtain the compound of formula II (132g), orange solid, content 97%. The yield is 99%.

[0075] (2) Stir dimethyl sulfide (1.2mol, 74.4g) and dimethyl sulfate (0.48mol, 60.5g) at 40°C for 4 hours, and then evaporate the dimethyl sulfide to dryness. At room temperature, the DMF (800 mL) solution of the compound of formula II (0.4 mol, 132 g) obtained in step (1) was added to...

Embodiment 3

[0078] The preparation method of epoxiconazole of this embodiment has the following steps:

[0079] (1) Add Br dropwise to the HOAc (180mL) solution of the compound of formula I (0.4mol, 100g) at 0°C 2 (0.44mol, 69.5g) in HOAc (20mL) solution. After the addition was completed, the reaction was carried out at room temperature for 2 hours. The reaction solution was concentrated and diluted with ethyl acetate solvent, and then washed with 10% by mass sodium sulfite solution and saturated sodium bicarbonate solution respectively, the organic phase was dried with anhydrous sodium sulfate and concentrated to obtain the compound of formula II (X =Br, 133g), orange solid, content 96%, yield 98%.

[0080] (2) Stir dimethyl sulfide (1.17mol, 72.5g) and dimethyl sulfate (0.47mol, 59.0g) at 40°C for 4 hours, then evaporate the dimethyl sulfide to dryness. At room temperature, to the resulting mixture was added the DMF (800 mL) solution of the compound of formula II (X = Br, 0.39 mol, 127 g) ...

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Abstract

The invention relates to an epoxiconazole intermediate, a preparation method thereof, and a preparation method of epoxiconazole. The epoxiconazole intermediate is a compound with a structural formulaIII shown in the description, and X in the formula III is Br or Cr. The preparation methods have the advantages of cheap and easily available raw materials, simple steps, high safety, few pollution ofthree wastes, mild reaction conditions, green, clean and environmentally-friendly reagents and reaction processes, suitableness for industrial production, and realization of high yield and high content of the final products.

Description

Technical field [0001] The invention belongs to the field of fungicides, and specifically relates to an epoxiconazole intermediate and a preparation method of epoxiconazole. Background technique [0002] Epiconazole is a systemic triazole fungicide. It has a good control effect on cereal crops such as powdery mildew, wilt and other diseases. It also has good effects on sugar beets, melons, peanuts, onions and garlic, rape, etc. Diseases such as kidney beans and fruit trees have good control effects. At present, there are mainly the following routes for the preparation of epoxiconazole: [0003] Route 1: [0004] [0005] Route 2: [0006] [0007] Route 3: [0008] [0009] Route 4: [0010] [0011] Existing methods often need to use phosphine reagents, Grignard reagents, peroxides and reducing agents, and there are many problems such as three wastes, unstable reaction reagents and high risk, which do not meet the requirements of environmental protection and are not conducive to indu...

Claims

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Application Information

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IPC IPC(8): C07D303/08C07D301/02C07D405/06
CPCC07D301/02C07D303/08C07D405/06
Inventor 安静刘玉超吴天宇陶亚春
Owner JIANGSU SEVENCONTINENT GREEN CHEM CO LTD
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