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Synthetic method of fipronil and analogues thereof

A synthesis method and analogue technology, applied in the field of synthesis of fipronil and its analogues, can solve the problems of difficult high-scale industrial application, low reaction rate, difficult to put into use, etc., and achieve less waste discharge and low cost , mild and concise reaction conditions

Pending Publication Date: 2019-09-20
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although ozone oxidation can not introduce other heteroatoms in this strategy, ozone needs to be prepared separately, and ozone is difficult to control as a gas, and it is difficult for high-scale industrial application; the third is to use hydrogen peroxide, trifluoroacetic acid, and water system for reaction [K.H.Gharda, A.M.Malte, P.C.Joseph, S.D.Parkar, S.V.Sathe, P.D.Damania, Gharda Chemicals Limited, India.2007, p.19pp.; L.V.Sokolenko, I.I.Maletina, L.M. Yagupolskii, Y.L.Yagupolskii, Synlett 2010-208, 207 .; V.L. Sokolenko, K.R. Orlova, A.A. Filatov, L.Y. Yagupolskii, E. Magnier, B. Pégot, P. Diter, Molecules 2019, 24.]
This type of strategy has a slight advantage over the first two strategies. However, in the synthesis of organic compounds, water is difficult to dissolve various substrates as a solvent, which also makes the reaction rate relatively low, so this type of method is difficult to put into use.
Therefore, for trifluoromethylthiosulfoxide compounds, mild, green, concise and efficient synthetic methodology research is extremely challenging and has application value

Method used

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  • Synthetic method of fipronil and analogues thereof
  • Synthetic method of fipronil and analogues thereof
  • Synthetic method of fipronil and analogues thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The synthesis of embodiment 1 fipronil

[0041]

[0042] Take a 25mL round bottom flask, first add 211mg of sulfide compound of formula (2), 204mg of trichloroacetic acid, 3mL of toluene, mix well, wait until the temperature of the system returns to the reaction temperature, generally 15-25°C, then add 30% peroxide Hydrogen 127μL, stirred at 20°C for 96 hours, to 19 The progress of the reaction was monitored by F-NMR. After the reaction, the system was filtered for solid-liquid separation, and the obtained solid column was chromatographed, and the developing agent was dichloromethane, and 156 mg of fipronil, the compound of formula (1), was separated to obtain 156 mg of the compound of formula (1), with a yield of 72%. 19 The content of sulfone in the reaction stock solution was detected by F-NMR, and the generation of sulfone could not be detected.

Embodiment 2

[0043] The synthesis of embodiment 2 fipronil

[0044] Take a 10mL reaction tube, add 211mg of sulfide compound of formula (2), 163mg of trichloroacetic acid, 0.41mL of 30% hydrogen peroxide, 2.5mL of toluene, and stir at 20°C for 48 hours. After the completion of the reaction, 171 mg of fipronil was obtained through column chromatography separation, with a yield of 78%. 19 The content of sulfone in the reaction stock solution was detected by F-NMR, and the generation of sulfone could not be detected.

Embodiment 3

[0045] The synthesis of embodiment 3 fipronil

[0046] Take a 10mL reaction tube, add 211mg of sulfide compound of formula (2), 327mg of trichloroacetic acid, 0.41mL of 30% hydrogen peroxide, 2.5mL of toluene, and stir at 20°C for 24 hours. After the end of the reaction, column chromatography separated to obtain 175 mg of fipronil, with a yield of 80%. 19 The content of sulfone in the reaction stock solution was detected by F-NMR, and the generation of sulfone could not be detected.

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Abstract

The invention discloses a method for synthesizing fipronil and analogues thereof. The fipronil and analogues thereof are shown as a formula (I). The synthesis method comprises the following steps: (a) mixing a thioether compound shown as a formula (II) with trichloroacetic acid and an aprotic organic solvent; (b) adding hydrogen peroxide into the mixture obtained in the step (a), and carrying out oxidation reaction, so as to obtain fipronil as shown in a formula (I) and analogues thereof; the substituents in the formula (I) and the formula (II) are defined in the specification. The novel synthetic method is simple in condition and easy for industrial production.

Description

technical field [0001] The invention belongs to but not limited to the field of organic synthetic chemistry, and in particular relates to a synthetic method of fipronil and its analogues. Background technique [0002] Trifluoromethylthiosulfoxide compounds, especially aryl trifluoromethylthiosulfoxide compounds, have significant biological activity and widely exist in the skeleton structure of pesticides (insecticides, such as: fipronil) compounds , Therefore, the research on the efficient synthesis of trifluoromethylsulfoxide compounds has important scientific significance and application value. [0003] However, the existing synthetic methodology is limited by the efficiency and selectivity of the oxidizing agent, and if the oxidizing agent is too strong, it is extremely easy to generate the over-oxidized by-product sulfone. Mild oxidation conditions will lead to a greatly prolonged reaction time or even no reaction. Moreover, using hydrogen peroxide as an oxidant to ach...

Claims

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Application Information

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IPC IPC(8): C07D231/44
CPCC07D231/44
Inventor 焦宁宋颂王申安魏佳良
Owner PEKING UNIV
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