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Synthesis method of bupirimate

A pyrithrimolsulfonate and synthetic method technology, applied in the direction of organic chemistry, can solve the problems of easy decomposition, floating reaction yield, large products, etc., and achieve the effect of stable yield and complete reaction of raw materials

Active Publication Date: 2020-11-13
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the deficiencies and defects in the prior art, the invention provides a synthetic method of pyrimetholsulfonate to solve the problem of pyrimethol preparation in the prior art In the pyrithrimol sulfonate reaction, the pyrithrimol reaction is incomplete, the reaction yield fluctuates greatly, and the product is easily decomposed in the system

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  • Synthesis method of bupirimate

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Experimental program
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Effect test

Embodiment 1

[0030] First, 100 g of pyrimol was dissolved in 200 ml of methanol, 19 g of sodium hydroxide was added, and the reaction was stirred at 25° C. for 1 hour. After stirring, methanol was evaporated to dryness. Afterwards, 300 mL of toluene and 82 g of N,N-dimethylsulfamoyl chloride were sequentially added to the reaction system, and the system was heated to reflux. After reacting for 8 hours, the toluene was evaporated to dryness, 300 mL of petroleum ether was added, the system was cooled to 0° C., and the product was stirred to precipitate; the product was centrifugally filtered, dried and weighed 143 g, and the yield was 95%.

[0031] 1 H NMR (500MHz, CDCl 3 )δ4.96(brs,0.9H),3.58-3.30(m,2H),3.05(s,6H),2.62-2.42(m,2H),2.34(s,3H),1.55-1.42(m,2H ),1.41-1.33(m,2H),1.21(t,J=7.2Hz,3H),0.94(t,J=7.2Hz,3H). 13 C NMR (126MHz, CDCl 3 )δ169.16, 163.16, 159.75, 110.43, 38.77, 36.40, 31.65, 24.73, 22.63, 21.83, 14.85, 13.90.

[0032] According to the above characterization data, it can...

Embodiment 2

[0034] First, 100 g of pyrimol was dissolved in 200 ml of ethanol, 51 g of sodium carbonate was added, and the reaction was stirred at 25° C. for 1 hour. After stirring, ethanol was evaporated to dryness. Afterwards, 300 mL of toluene and 82 g of N,N-dimethylsulfamoyl chloride were sequentially added to the reaction system, and the system was heated to reflux. After reacting for 8 hours, evaporate toluene to dryness, add petroleum ether 300mL, cool the system to 0°C, stir and precipitate the product; the product is filtered, dried and weighed 147g, which is pyrimetholsulfonate with a yield of 97%.

Embodiment 3

[0036] First, 100 g of pyrimol was dissolved in 200 ml of ethanol, 26 g of sodium methoxide was added, and the reaction was stirred at 25° C. for 1 hour. After stirring, ethanol was evaporated to dryness. Afterwards, 300 mL of toluene and 82 g of N,N-dimethylsulfamoyl chloride were sequentially added to the reaction system, and the system was heated to reflux. After reacting for 8 hours, evaporate the toluene to dryness, add petroleum ether 300mL, cool the system to 0°C, stir and precipitate the product; the product is centrifugally filtered, dried and weighed 140g, which is pyrimolsulfonate with a yield of 93%.

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Abstract

The invention discloses a synthesis method of bupirimate. The method comprises the following steps: dissolving ethirimol in a polar solvent, adding alkali into the solution, and stirring to react for1-2 hours; after stirring is finished, evaporating the polar solvent to dryness, adding an organic solvent and N,N-Dimethylsulfamoyl chloride into a reaction system, heating the system for reflux reaction, and evaporating the organic solvent to dryness after the reaction is finished; adding petroleum ether into the system, cooling the system to-5 DEG C to 0 DEG C, stirring to separate out a product, and filtering to obtain the bupirimate. According to the preparation method disclosed by the invention, through a strategy of salifying the ethirimol and then reacting the ethirimol with the N,N-Dimethylsulfamoyl chloride, the problems of incomplete ethirimol reaction, unstable reaction yield and easiness in product decomposition due to the fact that HCl generated in the reaction cannot be fully neutralized are avoided; the problem that the ethirimol cannot be completely converted due to the fact that the N,N-Dimethylsulfamoyl chloride is decomposed by adding water into the system is also avoided, so that the synthesis method is complete in raw material reaction, stable in yield and more suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of pyrithrimol sulfonate synthesis, and in particular relates to a synthetic method of pyrithrimol sulfonate. Background technique [0002] Ethyrimol sulfonate is an adenosine deaminase inhibitor, mainly used for the treatment of plant powdery mildew. The key step in the synthesis of pyrithrimol sulfonate is the conversion of pyrithrimol to pyrithrimol sulfonate. This step reaction is the last step in the synthesis of pyrimolsulfonate, and the amount of by-products directly affects the aftertreatment and purification of the reaction. On the other hand, pyrimol and N,N-dimethylsulfamoyl chloride are expensive, which have a greater impact on the cost of raw materials for the reaction. Therefore, the efficient and high-yield conversion of pyrithrimol to pyrithrimol sulfonate is very important. [0003] The conversion of pyrithrimol to pyrithrimol sulfonate reported in the literature is achieved by directly h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/47
CPCC07D239/47
Inventor 苏天铎戎豪杰徐泽刚陈涛杨翠凤
Owner XIAN MODERN CHEM RES INST