Synthesis method of sulfentrazone intermediate

A synthesis method and technology of sulfentrazone are applied in the field of synthesis of sulfentrazone intermediates, can solve the problems of hazardous waste of sodium chloride, cannot be used well for downstream production, increase production cost, etc., and achieve good energy saving, The effect of avoiding supply constraints and improving production efficiency

Active Publication Date: 2021-09-17
SHANDONG WEIFANG RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Not only that, the isomers and other chlorinated products produced during the production of 2,4-dichloroaniline cannot be well used in downstream production; the oxidation process uses sodium hypochlori

Method used

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  • Synthesis method of sulfentrazone intermediate
  • Synthesis method of sulfentrazone intermediate
  • Synthesis method of sulfentrazone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Synthesis of 1-(2,4-dichlorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one

[0080] The reaction scheme is as follows:

[0081]

[0082] The specific synthesis method is as follows:

[0083] The first step: Chlorobenzene nitration reaction

[0084] The mixture of 300.0g chlorobenzene and 214.0g sulfuric acid nitric acid containing 30% nitric acid was added in the adiabatic nitration reactor, and the adiabatic reaction was started at 25° C. for 1 hour. When the temperature began to drop, the reaction ended. Separation of spent acid, sodium bicarbonate washing to neutrality, decompression distillation to remove chlorobenzene, reclaim chlorobenzene can be recycled, after obtaining o-chloronitrobenzene, p-chloronitrobenzene mixture 150.5g, content 99% (including o-chloronitrobenzene Para-isomer), hereinafter referred to as nitration product I.

[0085] The second step: hydrogenation reduction reaction

[0086] Add 157.5g of nitration product I to 500ml of methanol, add ...

Embodiment 2

[0098] Synthesis of 1-(2,4-dichlorophenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-one

[0099] The reaction scheme is as follows:

[0100]

[0101] The specific synthesis method is as follows:

[0102] The first step: Chlorobenzene nitration reaction

[0103] The mixture of 300.0g chlorinated benzene and 214.0g sulfuric acid nitric acid containing 30% nitric acid was added in the adiabatic nitration reactor, and the adiabatic reaction was started at 25° C. for 1 hour. When the temperature began to drop, the reaction ended. Separation of spent acid, sodium bicarbonate washing to neutrality, decompression distillation to remove chlorobenzene, reclaim chlorobenzene can be recycled, after obtaining o-chloronitrobenzene, p-chloronitrobenzene mixture 150.5g, content 99% (including o-chloronitrobenzene Para-isomer), hereinafter referred to as nitration product I;

[0104] The second step: hydrogenation reduction reaction

[0105] Add 157.5g of nitrated product I to 500ml of methanol,...

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Abstract

The present invention provides a synthesis method of asulfentrazone intermediate. The methodcomprises: S1) carrying out a nitration reaction on chlorobenzene in a nitration reagent to obtain a mixture of o-chloronitrobenzene and p-chloronitrobenzene, wherein the product does not need to be separated; s2) performing catalytic hydrogenation reaction on the mixture of o-chloronitrobenzene and p-chloronitrobenzene to obtain a mixture of o-chloroaniline and p-chloroaniline, wherein the product does not need to be separated; s3) making the mixture of o-chloroaniline and p-chloroaniline subjected to a diazotization reaction to obtain a mixture of o-chlorophenylhydrazine and p-chlorophenylhydrazine, wherein the product does not need to be separated; s4) performing condensation reaction on the mixture of the o-chlorophenylhydrazine and the p-chlorophenylhydrazine and aldehyde to obtain triazole ring mixtures as shown in a formula I-a and a formula I-b; and S5) carrying out chlorination reaction on the triazole ring mixtures to obtain the sulfentrazone intermediate shown in the formula I. According to the method, 2, 4-dichloroaniline is not used as a raw material, so that the production cost of sulfentrazone is reduced, and the limitation of raw material supply is avoided.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of a sulfentrazone intermediate. Background technique [0002] Sulfentrazone is a herbicide of difluoromethyltriazolinone class, the chemical name is N-(2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro- 3-Methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide, its chemical structural formula is as follows: [0003] [0004] The benzotriazolinone derivatives substituted by the 5-amino group on the benzene ring are very important pesticide intermediates. Among them, 1-(2,4-dichlorophenyl)-3-methyl-1H-1 ,2,4-triazol-5(4H)-one is the core intermediate in the synthesis of sulfentrazone. Its structural formula is as follows: [0005] [0006] The existing synthesis method of triazolinone intermediates usually takes aniline as the starting material, obtains the corresponding hydrazine through diazotization reduction, then condenses with aldehyde ...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07D249/12Y02P20/584
Inventor 李志清夏雨刘强荆双勇赵广理
Owner SHANDONG WEIFANG RAINBOW CHEM
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