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Method for preparing chlorfenapyr and analog thereof

An analog, the technology of chlorfenapyr, which is applied in the field of preparation of chlorfenapyr and its analogs, can solve the problems that triethylamine cannot be directly applied mechanically, the acid binding agent is expensive, the recovery rate is not high, etc., and achieves good industrial application prospects, The effect of low production cost and high reaction yield

Active Publication Date: 2009-12-02
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as Journal of Organic Chemistry, 49 (1) p.203 (1984), US 5151536 introduction is acid binding agent with sodium hydrogenate; US5010098 then is acid binding agent with sodium tert-butoxide; But these acid binding agents are comparatively expensive, and Certainly dangerous, the solvent tetrahydrofuran used is also relatively expensive, and the recovery rate is not high
US5359090 uses triethylamine as the acid-binding agent and toluene as the solvent, which solves the aforementioned problems preferably. It is a commonly used production method at present. distillation

Method used

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  • Method for preparing chlorfenapyr and analog thereof
  • Method for preparing chlorfenapyr and analog thereof
  • Method for preparing chlorfenapyr and analog thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 35 grams of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile, 8 grams of sodium hydroxide, and 200 ml of methyl isobutyl methyl ketone into the there-necked flask, stir for 20 minutes, Add 20 grams of chloromethyl ethyl ether dropwise, raise the temperature to 60°C, and react at this temperature for 2 hours, take a sample to monitor, the reaction is complete, cool down to room temperature, add 200ml of water, adjust the pH to <7 with 10% dilute hydrochloric acid, Layering, precipitation, and drying yielded 45.0 g of chlorfenapyr technical. Content 90%, yield 99%. 150ml of 80% tert-butanol was added to the precipitated material for recrystallization to obtain 38 grams of 98% chlorfenapyr as the original drug.

Embodiment 2

[0026] Add 35 grams of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile, 12 grams of potassium hydroxide, and 200 ml of methyl isobutyl methyl ketone into the there-necked flask, and stir for 20 minutes. Add 20 grams of chloromethyl chloroethyl ether dropwise, raise the temperature to 55°C, and react at this temperature for 1 hour, take a sample to monitor, the reaction is complete, cool down to room temperature, add 200ml of water, and adjust the pH to 5 with 10% dilute hydrochloric acid , layered, precipitated, added 150ml of 80% ethanol for recrystallization, and obtained 42.0 g of the original drug of HNPC-A3061 with a content of 98%.

Embodiment 3

[0028] Add 35 grams of 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile, 9 grams of sodium hydroxide, and 200 ml of cyclohexanone into the three-necked flask, stir for 20 minutes, and add dropwise 20 gram of chloromethyl chloroethyl ether, warming up to 40°C, and reacting at this temperature for 3 hours, taking samples for monitoring, the reaction was complete, cooling down to room temperature, adding 200ml of water, adjusting the pH to 5 with 10% dilute hydrochloric acid, and layering , precipitation, adding 150ml of 80% methanol for recrystallization to obtain the original drug of HNPC-A3061.

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Abstract

The invention discloses a method for preparing chlorfenapyr and analog thereof by using 4-bromo-2-(4-chlorphenyl)-5-trifluoromethylpyrrole-3-nitrile and chloromethyl ether as raw materials in the presence of ketones solvent and inorganic alkali acid-binding agent. The chemical reaction formula is as above. The method for synthesizing the chlorfenapyr and the analog thereof by adopting the ketones solvent and the inorganic alkali acid-binding agent has the advantages of simple process, mild reaction condition, low production cost and the like, and has good industrial application prospect.

Description

technical field [0001] The present invention relates to a preparation method of chlorfenapyr and its analogues, especially by using 4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile as raw material, in ketone A method for preparing chlorfenapyr and its analogues in the presence of quasi-solvents and inorganic base acid-binding agents. Background technique [0002] Chlorfenapyr, also known as Chujin, chlorfenapyr, chemical name 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-trifluoromethylpyrrole-3-carbonitrile , the chemical structural formula is: [0003] [0004] Chlorfenapyr is a new type of heterocyclic insecticide, acaricide and nematocide successfully developed by American Cyanamid Corporation. Chlorfenapyr has the advantages of fast insecticidal speed, wide insecticidal spectrum, thorough control and long control time. Years of field tests and practical applications have shown that it has excellent control effects on more than 70 kinds of pests i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
Inventor 陶贤鉴黄超群熊莉莉罗亮明庞怀林杨剑波
Owner HUNAN CHEM RES INST
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