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Synthesis method of indoxacarb intermediate semicarbazone

A technology of semicarbazone and synthetic method, which is applied in the field of synthesis of indoxacarb intermediate semicarbazone, can solve the problems of reduced yield, carbon-nitrogen double bond breakage, high toxicity, etc., and avoid high cost, Good safety, economy and high yield

Active Publication Date: 2017-07-07
JIANGSU YOUJIA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the process of the acid-catalyzed ring-closure of the compound shown in the intermediate formula 6 of the route two to generate indoxacarb, the carbon-nitrogen double bond is prone to breakage, so that the yield of this step is greatly reduced; in the route three, the conversion of the compound shown in the formula 5 Need to use 4-trifluoromethoxyphenyl isocyanate in the process to the compound shown in formula 7, and synthetic isocyanate needs to use the bigger phosgene product of toxicity

Method used

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  • Synthesis method of indoxacarb intermediate semicarbazone
  • Synthesis method of indoxacarb intermediate semicarbazone
  • Synthesis method of indoxacarb intermediate semicarbazone

Examples

Experimental program
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Effect test

Embodiment 1

[0030] A kind of synthetic method of indoxacarb intermediate semicarbazone, concrete steps are as follows:

[0031] (1), add 17.7g (0.1mol) 4-trifluoromethoxyaniline, 50mL acetic acid and 100mL water successively in 500mL four-neck flask under nitrogen protection; 14.4g (0.22mol) mass fraction is 90% Dissolve sodium isocyanate in 40mL of acetic acid and 100mL of water, add the sodium isocyanate solution dropwise to the 4-trifluoromethoxyaniline solution in an ice-water bath, raise the temperature to 20°C, stir and react for 12 hours, and analyze in the central control The conversion rate of 4-trifluoromethoxyaniline was 97%, then cooled to 0-5°C and kept for 2 hours, and suction filtered to obtain off-white solid 4-trifluoromethoxyphenylurea with a yield of 85%;

[0032] (2), in a 250ml four-necked flask equipped with a condenser, add 10.5g (48mmol) of p-trifluoromethoxyphenyl urea obtained in step 1, 5.7g (144mmol) of hydrazine hydrate with a mass fraction of 80% , 50mL of e...

Embodiment 2

[0035] A kind of synthetic method of indoxacarb intermediate semicarbazone, concrete steps are as follows:

[0036](1), under nitrogen protection, add 34g (0.2mol) 4-trifluoromethoxyaniline, 100mL acetic acid and 200mL water successively in 1L four-neck flask; Dissolve potassium cyanate in 80mL acetic acid and 200mL water, add the potassium isocyanate solution dropwise to the 4-trifluoromethoxyaniline solution in an ice-water bath, heat up to 30°C and stir for 24 hours. The central control analysis 4- The conversion rate of trifluoromethoxyaniline was 99%, and then cooled to 0-5° C. for 1 hour, and suction filtered to obtain off-white solid 4-trifluoromethoxyphenylurea, with a yield of 85%;

[0037] (2), in a 250ml four-necked flask equipped with a condenser, add 10.5g (48mmol) of p-trifluoromethoxyphenyl urea obtained in step 1, 5.7g (144mmol) of hydrazine hydrate with a mass fraction of 80% , 50mL of ethanol, and then heated up to 80°C for reflux, reflux for 24 hours, and t...

Embodiment 3

[0040] A kind of synthetic method of indoxacarb intermediate semicarbazone, concrete steps are as follows:

[0041] (1), add 17.7g (0.1mol) 4-trifluoromethoxyaniline, 50mL acetic acid and 100mL water successively in 500mL four-neck flask under nitrogen protection; 14.4g (0.22mol) mass fraction is 90% Dissolve sodium isocyanate in 40mL of acetic acid and 100mL of water, add the sodium isocyanate solution dropwise to the 4-trifluoromethoxyaniline solution in an ice-water bath, heat up to 25°C and stir for 12 hours. - The conversion rate of trifluoromethoxyaniline is 95%, then cooled to 0-5°C and kept for 2 hours, and suction filtered to obtain off-white solid 4-trifluoromethoxyphenylurea, with a yield of 85%;

[0042] (2) In a 250ml four-necked flask equipped with a condenser, add 10.5g (48mmol) of p-trifluoromethoxyphenyl urea obtained in step 1 and 5.7g (144mol) of hydrazine hydrate with a mass fraction of 80%. , 50mL of ethanol, then heated up to 80°C for reflux, reflux for ...

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Abstract

The invention discloses a synthesis method of an indoxacarb intermediate semicarbazone. The synthesis method includes the steps of producing 4-trifluoromethoxy phenylurea from 4-trifluoromethoxyaniline and isocyanate under the action of acetic acid; enabling the 4-trifluoromethoxy phenylurea and hydrazine hydrate to undergo hydrazinolysis in an organic solvent so as to obtain 4-trifluoromethoxy phenylamino hydrazide; enabling the 4-trifluoromethoxy phenylamino hydrazide and 5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-indene-2-carboxylic acid methyl ester in an organic solvent under the action of a catalyst. The synthesis method has the advantages that the intermediate semicarbazone is synthesized from industrially available isocyanate through a series of conversion, and accordingly the synthesis method is free of toxic substances and phosgene products and capable of avoiding the shortcomings of high cost and low yield when precious metals serve as catalysts as well as overcoming the technical defect of low ring-closure reaction yield; the synthesis method is high in safety and is economical and high in yield when used for synthesizing indoxacarb atoms.

Description

technical field [0001] The invention relates to a synthesis method of an indoxacarb intermediate, in particular to a synthesis method of an indoxacarb intermediate semicarbazone. Background technique [0002] Indoxacarb is the first commercial oxadiazine sodium ion channel blocking chiral insecticide, and its chemical name is 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl) [4-(Trifluoromethoxy)-phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester. Indoxacarb has the characteristics of novel structure, unique mechanism of action, low dosage, effective against almost all Lepidoptera pests and safe for humans, the environment, crops and non-target organisms; in addition, it has a short time limit before crop harvesting, and is suitable for The integrated pest management system is one of the ideal varieties to replace organophosphorus insecticides, and has become a research hotspot and a pesticide variety that has received widespread attention. ...

Claims

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Application Information

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IPC IPC(8): C07C281/12
CPCC07C273/1809C07C281/06C07C281/12C07C275/34
Inventor 周其奎姜友法黄成美丁超吕杨薛亚东
Owner JIANGSU YOUJIA CHEM
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