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Preparation method of pyroxasulfone and intermediate thereof

A technology of sulfofenapyr and an intermediate, which is applied in the field of preparation of sulfofenapyr and its intermediates, can solve the problems of low yield of sulfofenazone, great harm to the environment and human beings, and teratogenicity of formaldehyde solvent. , to achieve the effect of high product purity, simplified production process and easy separation

Active Publication Date: 2021-12-07
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007]In the above-mentioned process route, the yield of pyrazoxazole is too low, and the formaldehyde water solvent is easy to cause teratogenicity, which is very harmful to the environment and human beings

Method used

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  • Preparation method of pyroxasulfone and intermediate thereof
  • Preparation method of pyroxasulfone and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1. Synthesis of Intermediate A:

[0041] Add 16.6 g of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, 3 g of paraformaldehyde, 8.5 g of piperidine, and 10 g of 37% hydrochloric acid aqueous solution in sequence in 40 mL of ethanol at room temperature, and heat Stir the reaction at 80°C for 4hrs, and add 5,5-dimethyl-3-mercapto-4,5 after no 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol is detected by HPLC -Dihydroisoxazole 21.6g, continue the reaction, continue to react for 4hrs, HPLC detects that the reaction of 5,5-dimethyl-3-mercapto-4,5-dihydroisoxazole is complete, after the reaction is completed, the ethanol is evaporated under reduced pressure , add 20mL of water to make a slurry for 2hr, suction filter to obtain a white solid precipitate, and dry to obtain 28.8g solid, which is Intermediate A. The purity measured by HPLC is 99.4%, and the yield is based on 1-methyl-3-(trifluoromethyl) -1H-pyrazol-5-ol was 92.6%.

[0042] 2. Synthesis of Intermediate B:

[0043] ...

Embodiment 2

[0047] 1. Synthesis of Intermediate A:

[0048] Add 33.2 g of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, 6 g of paraformaldehyde, 14.2 g of pyrrole, and 20 g of 37% hydrochloric acid aqueous solution in sequence in 80 mL of ethanol at room temperature, and heat to Stir the reaction at 75°C for 4 hours, and add 5,5-dimethyl-3-mercapto-4,5- Dihydroisoxazole 43.2g, continue to react, after continuing to react for 4hrs, HPLC detects that the reaction is over, the reaction solution is evaporated under reduced pressure to remove ethanol, 20mL of water is added to make a slurry for 2hr, and a white solid is precipitated by suction filtration, and dried to obtain 57.5g of solid, which is The purity of intermediate A measured by HPLC was 99.2%, and the yield was 92.3% based on 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol.

[0049] 2. Synthesis of Intermediate B:

[0050] Add 10.6g of sodium carbonate and 30.9g of intermediate A to 40mL of acetonitrile, stir at 20°C for 2hrs, slowl...

Embodiment 3

[0054] Synthesis of Intermediate A:

[0055] Add 33.2 g of 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, 6 g of paraformaldehyde, 17.4 g of morpholine, and 20 g of 37% hydrochloric acid aqueous solution in sequence in 80 mL of ethanol at room temperature, and heat Stir the reaction at 60°C for 4hrs, and add 5,5-dimethyl-3-mercapto-4,5 after no 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol is detected by HPLC -Dihydroisoxazole 43.2g, continue to react, continue to react for 4hrs, HPLC detects that the reaction is over, evaporate ethanol under reduced pressure after the reaction, add 20mL water for beating for 2hrs, suction filter to obtain a white solid precipitate, and dry to obtain 56.8g solid, which is The purity of Intermediate A measured by HPLC was 99.3%, and the yield was 91.3% based on 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol.

[0056] 2. Synthesis of Intermediate B:

[0057] Add 10.6g of sodium carbonate and 30.9g of intermediate A to 40mL of acetonitrile, stir at...

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Abstract

The invention discloses a preparation method of pyroxasulfone and an intermediate thereof, 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-alcohol, paraformaldehyde, cyclic secondary amine and 5, 5-dimethyl-3-sulfydryl-4, 5-dihydroisoxazole are subjected to mannich reaction in an acid environment to obtain an intermediate A, the intermediate A continues to be alkylated with monochlorodifluoromethane to obtain an intermediate B, and the intermediate B is oxidized by hydrogen peroxide to obtain pyroxasulfone. The route reaction speed is high, the product purity is high, the yield is high, the reaction condition is mild, the synthesis process is extensive, the equipment cost of the reaction is reduced, the produced product is easy to separate, and the production process is simplified.

Description

technical field [0001] The present invention relates to a kind of preparation method of metazazol sulfone intermediate, in particular to a method using 1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-ol, paraformaldehyde, ring secondary amine and 5,5-dimethyl-3-mercapto-4,5-dihydroisoxazole to synthesize the method of metazazole sulfone intermediate A, as well as the method for synthesizing metazazone sulfone through the new process route, which belong to sulfone The technical field of metazazole synthesis. Background technique [0002] Pyroxasulfone is an isoxazole herbicide, researched and developed by Japan Combination Chemical Co., Ltd., the chemical name is 3-[5-(difluoromethoxy)-1-methyl-3-( Trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-isoxazole, the molecular formula is C 12 h 14 f 5 N 3 o 4 S, the molecular weight is 391.32, and the CAS accession number is 447399-55-5. Metrafenazole can be used as a pre-emergent soil treatment agent in mo...

Claims

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Application Information

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IPC IPC(8): C07D413/12
CPCC07D413/12
Inventor 郝守志宋健王嵩
Owner SHANDONG RUNBO BIOTECH CO LTD
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