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A kind of preparation method of sulfentrazone

A technology of sulfentrazone and mesylate, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve high energy consumption and reaction time Long, low product yield and other issues

Active Publication Date: 2021-07-06
SHANDONG WEIFANG RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These two processes have disadvantages such as high energy consumption, long reaction time, high pressure safety risk, and low product yield.

Method used

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  • A kind of preparation method of sulfentrazone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 4.0g of dimethyl sulfide to 40g of dichloromethane, cool down to -5~0°C, start to pass chlorine gas, and pass in 4.2g of chlorine gas for about 1h, and stir at this temperature for 30min after passing through, as a catalyst Refrigerate and set aside.

Embodiment 2

[0038] Add 4.0g dimethyl sulfide to 40g dichloromethane, cool down to -5~0℃, start to add bromine water (Br 2 The molar ratio of dimethyl sulfide to dimethyl sulfide is 1:1), after passing through, stir at this temperature for 60 minutes, and use it as a catalyst for refrigerated use.

Embodiment 3

[0040] In a 250ml four-neck flask, dissolve 15.6g (0.05mol) of triazolone aniline in 50g of dichloromethane, lower the temperature to 0-5°C, add the catalyst of Example 1, and make dimethyl sulfonium chloride The mass is 5% of the mass of triazolone aniline, stirred for 30min; then 6.7g of methyl methanesulfonate was added dropwise at this temperature, and after the dripping was completed, the raw materials basically reacted completely at this temperature for 3h; The liquid was cooled to 0°C, suction filtered, and dried to obtain 19.3 g of sulfentrazone as a solid, the content of which was 99.1% as determined by HPLC, and the yield was 98.8%. The filtered mother liquor was distilled, and dichloromethane and methanol were recovered in sections.

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Abstract

The invention discloses a preparation method of sulfentrazone. The sulfentrazone is obtained from the reaction of triazolone aniline and methylsulfonate in the presence of a catalyst; the catalyst is a halogenated dimethyl sulfonium halide . The invention improves the reaction system, replaces methanesulfonyl chloride with stable and easy-to-storage methanesulfonyl chloride, avoids the use of highly corrosive methanesulfonyl chloride, triethylamine and pyridine, and does not generate salty wastewater , conducive to environmental protection. The amino compound is activated by a specific catalyst, so that side reactions are less, the amount of raw materials is less, and the yield and content are improved.

Description

technical field [0001] The invention relates to a method for preparing sulfentrazone, in particular to a method for preparing sulfentrazone by using triazolinone aniline and methylsulfonate under the catalysis of a catalyst. 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 traditional synthesis method of sulfentrazone is: use 2,4-dichloroaniline as raw material, undergo diazotization, condensation, N-alkylation, nitration, reduction, and amidation to obtain sulfentrazone, the reaction formula is as follows : [0005] . [0006] U.S. Patent No. 4,818,275 uses the above-mentioned route to synthesize sulfentrazone. In the synthetic method, the final amidation step is to use triazolone aniline and methanesulfonyl chloride a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12B01J31/02
CPCB01J31/0232C07D249/12
Inventor 孙国庆侯永生徐延磊赵广理宋新科
Owner SHANDONG WEIFANG RAINBOW CHEM
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