Synthesis method of mefenpyr-diethyl

A technology for the synthesis of mefenpyr-ethyl and the synthesis method, which is applied in the field of synthesis of mefenpyr-ethyl, can solve the problems of long synthetic route, high cost and low yield, and achieve short reaction route, low cost and high yield Effect

Active Publication Date: 2019-07-12
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The technical problem to be solved by the present invention is to provide a kind of synthetic method of mefenpyr-ethyl, so as to overcome the defects of long synthetic route, low yield and high cost of mefenpyr-ethyl in the prior art.

Method used

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  • Synthesis method of mefenpyr-diethyl

Examples

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Embodiment 1

[0040] Synthesis of ethyl 2-[2-(2,4-dichlorophenyl)hydrazinomethylene]acetate:

[0041] 2,4-Dichlorophenylhydrazine hydrochloride (21.3g, 0.1mol) was dissolved in 200ml of ethanol, triethylamine (10.1g, 0.1mol) was added, and 50% ethyl glyoxylate in toluene was added dropwise (40.8g, 0.2mol), the addition was completed in 30 minutes, the temperature was raised to reflux and stirred for 4 hours after the addition, the solvent was evaporated under reduced pressure, and the anhydrous ethanol was recrystallized to obtain 2-[2-(2,4-dichlorophenyl)hydrazino Methyl]ethyl acetate 16.1g, yield: 62%.

Embodiment 2

[0043] Synthesis of ethyl 2-[2-(2,4-dichlorophenyl)hydrazinomethylene]acetate:

[0044]Dissolve 2,4-dichlorophenylhydrazine hydrochloride (21.3g, 0.1mol) in 200ml tetrahydrofuran, add triethylamine (12.1g, 0.12mol), and add dropwise 50% ethyl glyoxylate in toluene (24.4g, 0.12mol), the addition was completed in 30 minutes, after the addition, the temperature was raised to reflux and stirred for 4 hours, the solvent was evaporated under reduced pressure, and recrystallized from absolute ethanol to obtain 2-[2-(2,4-dichlorophenyl)hydrazino Methyl]ethyl acetate 15.1g, yield: 58%.

Embodiment 3

[0046] Synthesis of pyraclofen-ethyl:

[0047] Add ethyl 2-[2-(2,4-dichlorophenyl)hydrazinomethylene]acetate (13.0 g, 0.05 mol) and ethyl methacrylate (6.8 g, 0.06 mol) into a 250 mL eggplant flask , add DMF (100mL) and stir to dissolve, then add molecular iodine (2.5g, 0.01mol) and 70% aqueous solution of TBHP (9.6g, 0.075mol) into the reaction system, react at room temperature for 8h, after the reaction is complete, add 100 ml of 10% aqueous sodium bisulfite. Extract with ethyl acetate (100mL×3), wash the ethyl acetate layer with saturated brine (100mL×2), distill off the solvent from the ethyl acetate layer under reduced pressure to obtain an oily liquid, and recrystallize from petroleum ether to obtain pyraclofen-ethyl 13.2 g, yield rate is 70%, mp: 48~51 ℃.

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Abstract

The invention relates to a synthesis method of mefenpyr-diethyl. The method comprises the steps of carrying out a reaction among 2,4-dichlorophenylhydrazine hydrochloride, ethyl glyoxalate and alkaliin a solvent, and carrying out a [3+2] cycloaddition reaction between obtained 2,4-dichlorophenylhydrazine ethyl glyoxylate hydrazone and ethyl methacrylate in a solvent under the function of a catalyst and an oxidant. According to the synthesis method, the starting raw materials are easy to obtain, the reaction time is shortened, the reaction path is short, the cost is low, the operation is simple, and three-waste treatment is lowered; under the same condition, the yield is higher, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of synthesis of mefenpyr-ethyl, in particular to a synthesis method of mefenpyr-ethyl. Background technique [0002] The molecular formula of Mefenpyr-diethyl is: C 16 h 18 Cl 2 N 2 o 4 , the English chemical name is 1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylic acid 3,5-diethyl ester, and the CAS registration number is: 135590-91 -9, the structural formula is: [0003] [0004] Metrafen-prop-ethyl is a new herbicide safener announced at the Brighton Plant Protection Conference in the UK in 1999. It can be used together with some herbicides such as methylsulfuron-methyl to protect crops such as wheat and barley from harm. Metrafenpyr-ethyl can also increase the resistance of wheat to methylsulfuron-methyl. (Gao Zongjun, Jiang Jiazhen, Li Xuefeng, Qiu Lihong, Wang Chengju, Zhang Wenji, Cheng Yuchen. Induction of pyraclopyr-methyl on wheat cytochrome P450 and its spectral characteris...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06
CPCC07D231/06
Inventor 赵圣印祝家楠王文康金泽慧林浩鹏
Owner DONGHUA UNIV
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