Synthetic method of (trifluoromethoxy) anisidine formylhydrazine

A technology of trifluoromethoxyanilinoformohydrazide and ethyl trifluoromethoxyanilinoformate is applied in the field of synthesis of intermediate p-trifluoromethoxyanilinoformohydrazide, which can solve the problem of high toxicity, Environmental pollution, low yield and other problems, to achieve the effect of reducing dosage, avoiding pollution, improving product quality and yield

Active Publication Date: 2012-07-18
JINGBO AGROCHEM TECH CO LTD
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AI Technical Summary

Problems solved by technology

[0005] At present, in China, methyl p-trifluoromethoxyaniline formate and hydrazine hydrate are mainly used as starting materials, and hydrazine hydrate is used as a reaction solvent. After the reaction is completed, direct filtration can produce p-trifluoromethoxyanisidine formyl Hydrazine, the reaction yield can only reach 90%. Hydrazine hydrate is also called hydrazine hydrate, which has strong alkalinity and hygroscopicity. However, this method has the advantages of high toxicity, environmental pollution and low yield due to the use of hydrazine hydrate as a solvent. shortcoming

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  • Synthetic method of (trifluoromethoxy) anisidine formylhydrazine
  • Synthetic method of (trifluoromethoxy) anisidine formylhydrazine

Examples

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Embodiment 1

[0023] Preparation of ethyl trifluoromethoxyanisole formate:

[0024] In a 250ml four-necked flask, add 17.7g of p-trifluoromethoxyaniline, 100ml of water, 8.5g of sodium bicarbonate, stir evenly, cool down to below 10°C, add 16g of ethyl chloroformate dropwise, and control the dropping rate , so that the temperature in the reaction bottle does not exceed 15 ° C, after 2 hours, the dropwise addition is completed. After raising the temperature to 20° C. for 4 hours of heat preservation reaction, the white product was obtained by filtration and dried to obtain 23.3 g of ethyl trifluoromethoxyaniline formate with a content of 96% and a yield of 95%.

[0025] Target product preparation:

[0026] In a 250 ml four-neck flask, add 25.9 g of ethyl p-trifluoromethoxyaniline formate, 18.75 g of 80 wt % hydrazine hydrate aqueous solution, and 133 g of dichloromethane, stir evenly, and add 0.3 g of tetrabutylammonium bromide. Heating to reflux, reacting for 5 hours, the reaction of p-tr...

Embodiment 2

[0028] In a 250 ml four-necked flask, add 25.9 g of ethyl p-trifluoromethoxyaniline formate, 6.25 g of 80 wt % hydrazine hydrate aqueous solution, 50 ml of chloroform, 0.8 g of tetrabutylammonium chloride, and heat to reflux After reacting for 8 hours, the reaction of p-trifluoromethoxy anilinate ethyl formate disappeared by liquid spectrum tracking, and the reaction ended;

[0029] Directly heat to distill chloroform, add 50g of water, cool down to 0°C, keep warm for 3 hours, and filter. The resulting product quality is 22.2g, and its content is 96wt% after detection, and its yield is calculated to be 95.5%.

Embodiment 3

[0031] In a 250 ml four-necked flask, add 25.9 g of ethyl p-trifluoromethoxyaniline formate, 80 wt % hydrazine hydrate aqueous solution 8 g, 330 g of dichloromethane, and 0.7 g of pyridine, heat to reflux and react for 10 hours. Follow the disappearance of the p-trifluoromethoxyanisole ethyl formate reaction, and the reaction ends;

[0032] Distill out dichloromethane by direct heating, add 250g of water, cool down to 10°C, keep warm for 2 hours, and filter. The resulting product quality is 23.3g, and its content is 96.5wt% after detection, and its yield is calculated to be 95.5%.

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Abstract

The invention belongs to the technical field of organic synthesis and particularly provides a method for synthesizing (trifluoromethoxy) anisidine formylhydrazine with a little amount of hydrazine hydrate as reactants, inexpensive organic solvents not mutually dissolving with water as reaction system solvents and phase transfer catalysts as catalysts. The synthetic method quickens reaction, improves product quality and yield, avoids highly virulent hydrazine hydrate pollution, and has the advantages of being high in yield, small in environment pollution and low in cost.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a synthesis technology of a pesticide intermediate, in particular to a synthesis method of metaflumizone intermediate p-trifluoromethoxyanilinoformohydrazide. Background technique [0002] The English name of metaflumizone is metaflumizone, chemical name: (E+Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene] -N-[4-(trifluoromethoxy)phenyl]-hydrazine oxalyl, its pure product is white solid powder. [0003] Metaflumizone is a semicarbazone insecticide with a unique mechanism of action. The drug mainly enters into the body of the pest to kill the pest through gastric poisoning, and the contact effect is small and has no systemic effect. The drug has a good control effect on the target pests and larvae of all ages. After the insects feed, the drug enters the insect body and blocks the sodium ion channel on the axon membrane of the pest neurons through a unique m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C281/06
Inventor 李洪侠綦菲刘英贤吴文雷高洪奎
Owner JINGBO AGROCHEM TECH CO LTD
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