Synthesizing method of sulfentrazone

A synthetic method, the technology of sulfentranacil, which is applied in the field of synthesis of sulfentrazone, can solve the problems affecting product quality and yield, strong corrosion of methanesulfonyl chloride, low yield of sulfentrazone, etc., and achieve the product The effect of good quality, high product yield and mild reaction conditions

Active Publication Date: 2019-01-18
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

2. Excessive triethylamine or pyridine produces a large amount of waste water, consumes 2 equivalents of methanesulfonyl chloride, the atom economy is poor, and the yield of sulfentrazone is low, the yield is only about 66%
U.S. Patent No. 5,990,315 discloses a method for catalyzing sulfonylation reactions using soluble salts such as quaternary ammonium salts and quaternary phosphonium salts. The method uses triazolinone aniline and methanesulfonyl chloride as raw materials to directly obtain sulfentrazone in one step. , this method solves the problem of direct sulfonylation, but there is still the p...

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  • Synthesizing method of sulfentrazone
  • Synthesizing method of sulfentrazone
  • Synthesizing method of sulfentrazone

Examples

Experimental program
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Effect test

Embodiment 1

[0031]Dissolve 17.6g of compound (II) in 88g of DMF, add 20.7g of potassium carbonate, raise the temperature to 140°C, and feed 10.5g of difluorochloromethane. After the reaction, cool down to room temperature and filter out the potassium salt; filter the filtrate at 20 Chlorine gas flow at ℃, and stop the chlorine gas flow when the central control is not turned to less than 1%. After the reaction, DMF is removed to obtain the intermediate (Ⅲ); 50% acetic acid aqueous solution is added to the intermediate (Ⅲ), and the temperature is raised to 80°C to start the flow. Chlorine gas, stop the chlorine gas when the central control is not turned to less than 1%, cool down, crystallize, filter and dry to obtain 25.6g of intermediate (Ⅳ), the content of which is 98.4% by GC.

[0032] Weigh 10g of intermediate (Ⅳ) and dissolve in acetic acid, add 0.05g of iodine, raise the temperature to 30°C, start to add 3.4g of bromine dropwise, control the dropping time between 2-3h, after the end, ...

Embodiment 2

[0035] Prepare sulfentrazone according to the method of Example 1, the difference is: the preparation process of the intermediate (Ⅴ) is: weigh 10g of the intermediate (Ⅳ) and dissolve it in 96% sulfuric acid, add 0.05g of iodine, and heat up to 30°C , start to add 3.4g of bromine dropwise, and control the dropping time between 2-3h. After the end, add 2.4g of hydrogen peroxide dropwise for 2-3h, keep warm for 1h after adding, add 30g of water, cool down, filter, wash, and dry , 12.5 g of intermediate (Ⅴ) was obtained, the content detected by HPLC was 97.8%, and the yield based on intermediate (Ⅳ) was about 98.1%.

Embodiment 3

[0037] Prepare sulfentrazone according to the method of Example 1, the difference is: the preparation process of the intermediate (Ⅴ) is: weigh 10g of the intermediate (Ⅳ) and dissolve it in 96% sulfuric acid, add 0.05g of iodine, and heat up to 60°C , start to add 3.4g of bromine dropwise, and control the dropping time between 2-3h. After the end, add 2.4g of hydrogen peroxide dropwise for 2-3h, keep warm for 1h after adding, add 30g of water, cool down, filter, wash, and dry 12.4 g of intermediate (Ⅴ) was obtained, the content detected by HPLC was 97.4%, and the yield based on intermediate (Ⅳ) was about 96.8%.

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Abstract

The invention discloses a synthesizing method of sulfentrazone. The synthesizing method comprises the following steps of using a compound (II) as the raw material, and performing difluoro methylation,chlorination and bromination; then, performing methylsulfonylation, so as to obtain the final product of the sulfentrazone. The synthesizing method has the advantages that the obtained intermediate after chlorination is firstly brominated, and then the obtained intermediate after bromination and the methanesulfonamide are catalyzed by a catalyst to obtain the sulfentrazone; the chemical selectivity is high, and the dangerous technologies of nitrification, hydrogenation and the like in the traditional technology route are avoided; the production of a large amount of waste acid and waste waterin the nitrification process is avoided, the green effect is better, the efficiency is higher, and the safety and reliability are higher; the whole technology is simple and convenient, and the reaction conditions are mild; by adjusting the reaction conditions, the yield rate of the obtained product is high, the quality of the product is high, and the synthesizing method is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing sulfentrazone, in particular to a method for synthesizing sulfentrazone with a brominated intermediate and methylsulfonamide 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 adopts the above-mentioned route to synthesize sulfentrazone. In this synthetic method, concentrated sulfuric acid is used as a solvent for nitration, and iron ...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 孙国庆侯永生徐延磊赵广理宋新科胡义山
Owner SHANDONG RUNBO BIOTECH CO LTD
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