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Preparation method of topramezone

A technology of fenflufen and a compound, which is applied in the field of preparation of fenflufen, can solve the problems of difficult operation, environmental hazards and high production costs, and achieves the effects of high reaction yield, economical production and less pollution

Inactive Publication Date: 2015-06-10
HEFEI JIUYI AGRI DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the carbon monoxide intercalation method requires the use of highly toxic carbon monoxide gas that is difficult to operate, high temperature and high pressure, and expensive palladium metal composite catalysts, which are high in production costs and difficult to operate; The highly toxic reagent acetone cyanohydrin is a rearrangement catalyst, and thionyl chloride needs to be used as an acid chloride reagent, and thionyl chloride is very harmful to the environment
[0003] In summary, both the carbon monoxide intercalation method and the rearrangement method after carboxylic acyl chloride esterification have low yield, high cost, and the production process contains highly toxic substances, which do not meet the requirements of large-scale industrial production.

Method used

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  • Preparation method of topramezone
  • Preparation method of topramezone
  • Preparation method of topramezone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Step a: take 1.5mol (36g) magnesium chips, 1.0mol (318g) 3-(3-bromo-2-methyl-6-methylsulfonylphenyl)-4,5-dihydroisoxazole (compound I ), 1000mL tetrahydrofuran was added to the reactor, then heated to 100°C and refluxed for 2 hours, the reaction solution was cooled to 0°C, and excessive carbon dioxide gas was passed into the reaction solution, (CO 2 The molar ratio with Compound I is 2-5: 1, that is, 2: 1, 3: 1, 4: 1, 5: 1, or any other ratio within this range), after continuing the incubation reaction for 10 hours , adjust the pH to weak acidity, cool and crystallize, filter, wash with water, and dry to obtain compound II, which weighs 242.5 g and yields 85.7%. Should

[0025] In the step, magnesium chips and part of compound I (eg, 5% of the total amount) can be added to a reactor containing a reaction solvent to initiate the reaction, and then the remaining compound I can be added to the reaction vessel.

[0026] Step b: Take 1 mol of compound II obtained from the ...

Embodiment 2

[0028] Step a: get 1.1mol (26.4g) magnesium chips, 1.0mol (318g) 3-(3-bromo-2-methyl-6-methylsulfophenyl)-4,5-dihydroisoxazole (compound 1), 1000mL1, 4-dioxane is added in the reactor, then heated to 120 ℃ and refluxed for 2 hours, the reaction solution is cooled to 0 ℃, and excess carbon dioxide gas (CO 2 The molar ratio with Compound I is 2-5:1, that is, 2:1, 3:1, 4:1, 5:1), after continuing the heat preservation reaction for 12 hours, adjust the pH to weak acidity, cool and crystallize, filter, and wash with water , and dried to obtain compound II, which weighed 235.5 g, and the yield was 83.2%.

[0029] Step b: Take 1 mol of compound II obtained from the above reaction, dissolve it in 1000 mL of dichloromethane, and then add 1.3 mol (127.4 g) of 1-methyl-5-hydroxypyridine at a temperature of 8-15 ° C within half an hour Azole (compound III) and 2mol (758g) of condensing agent HBTU and 2mol (212g) of sodium carbonate were stirred and reacted at a temperature of 8-15°C for ...

Embodiment 3

[0031] Take 1.3mol (31.2g) magnesium chips, 1.0mol (318g) 3-(3-bromo-2-methyl-6-methylsulfophenyl)-4,5-dihydroisoxazole (compound I), Add 1000mL tetrahydrofuran into the reactor, then heat to 80°C and reflux for 2 hours, then cool the reaction solution to 0°C, add 4.0mol (176g) dry ice to the reaction solution, and continue the reaction for 11 hours, then adjust the pH to weak acidity, Cool to crystallize, filter, wash with water, and dry to obtain compound II, which weighs 248.6 g and yields 87.8%.

[0032] Step b: Take 1 mol of compound II obtained from the above reaction, dissolve it in 1000 mL of dichloroethane, and then add 1.5 mol (147 g) of 1-methyl-5-hydroxypyridine at a temperature of 15-20 ° C within half an hour Azole (compound III) and 3mol (405g) of condensing agent HOBT and 3mol (222g) of calcium hydroxide were stirred and reacted at a temperature of 15-20°C for 8 hours, then washed with water, concentrated under reduced pressure, added methanol, beating with alc...

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Abstract

The invention discloses a preparation method of topramezone. The preparation method comprises the following steps: reacting carbon dioxide with 3-(3-bromine-2-methyl-6-methylsulfophenyl)-4,5-dihydro-isoxazole to generate 3-(4,5-dihydroisoxazole-3-yl)-2-methyl-4-methylsulfonylbenzoic acid, condensing and rearranging the generated 3-(4,5-dihydroisoxazole-3-yl)-2-methyl-4-methylsulfonylbenzoic acid and 1-methyl-5- hydroxy pyrazole to prepare the topramezone. The preparation method of the topramezone provided by the invention overcomes the defects that carbonic oxide highly toxic gas in a carbonic oxide carbonyl insertion method is difficult to operate, and a dear catalyst is needed, also overcomes the defect that a rearranging method after carboxyl acylation forms ester needs highly toxic catalyst acetone cyanalcohol, is low in cost, easy to operate, less in pollution, safe, environmentally friendly and the like, and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a preparation method of fenpyrazone. Background technique [0002] Tofenpyrazone is a kind of herbicide with high activity, low dosage and relatively safe so far. Its industrial preparation methods mainly include carbon monoxide intercalation method and rearrangement method after carboxylic acyl chloride forming ester, and the two methods are obtained The yield of finished product is lower. Among them, the carbon monoxide intercalation method requires the use of highly toxic carbon monoxide gas that is difficult to operate, high temperature and high pressure, and expensive palladium metal composite catalysts, which are high in production costs and difficult to operate; The highly toxic reagent acetone cyanohydrin is the rearrangement catalyst, and thionyl chloride needs to be used as the acid chloride reagent, and thionyl chloride is very harmful to the environ...

Claims

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Application Information

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IPC IPC(8): C07D413/10
CPCC07D413/10
Inventor 沈运河熊国银余正莲
Owner HEFEI JIUYI AGRI DEV
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