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Preparation method of phosphorothioate compound

A technology of phosphorothioate and thiosulfonyl compound, which is applied in the field of preparation of phosphorothioate compounds, can solve problems such as high cost, and achieve the effects of mild reaction, short reaction time and low preparation cost

Active Publication Date: 2019-12-13
YICHUN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods require expensive transition metal catalysts, oxidizing agents, or foul-smelling mercaptans

Method used

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  • Preparation method of phosphorothioate compound
  • Preparation method of phosphorothioate compound
  • Preparation method of phosphorothioate compound

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preparation example Construction

[0029] The present invention provides a kind of preparation method of phosphorothioate compound, and its steps are as follows:

[0030] A method for preparing phosphorothioate compounds, the steps of which are as follows: under the action of oxygen in the air and at a temperature of 60-80°C, copper salt is used as a catalyst, and thiosulfonyl compounds and diphenylphosphine oxide The compound was reacted in an organic solvent for 12 hours, and then the organic solvent was removed by rotary evaporation, and the residue was dissolved in dichloromethane, and then separated and purified by silica gel column chromatography to obtain phosphorothioate compounds.

Embodiment 1

[0034] In the air atmosphere, add 62.5mg (0.25mmol) of phenylthiobenzenesulfonate, 101mg (0.5mmol) of diphenylphosphine oxide, 4.76mg (0.025mmol) of CuI and 1ml of acetonitrile solvent into the round bottom flask, at temperature React at 60°C for 12 hours. After the reaction, use a rotary evaporator to spin off the acetonitrile solvent, and dissolve the residue with 1 mL of dichloromethane. The residue is separated and purified by silica gel column chromatography to obtain a white solid of phenylthiodiphenylphosphate , The calculated yield was 62%.

Embodiment 2

[0036] In the air atmosphere, add 62.5mg (0.25mmol) of phenylthiobenzenesulfonate, 101mg (0.5mmol) of diphenylphosphine oxide, 2.48mg (0.025mmol) of CuCl and 1ml of acetonitrile solvent into the round bottom flask, at temperature React at 60°C for 12 hours. After the reaction, use a rotary evaporator to spin off the acetonitrile solvent, and dissolve the residue with 1 mL of dichloromethane. The residue is separated and purified by silica gel column chromatography to obtain a white solid of phenylthiodiphenylphosphate , The calculated yield was 54%.

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Abstract

The invention discloses a preparation method of a phosphorothioate compound. The preparation method comprises the following steps: under the action of oxygen in air and at the temperature of 60-80 DEGC, taking a copper salt as a catalyst, reacting a thiosulfonyl compound with a diphenyl phosphine oxide in an organic solvent, and performing rotary evaporation treatment and silica gel column chromatography separation and purification to obtain the phosphorothioate compound. The phosphorothioate compound is synthesized by taking the thiosulfonyl compound and the diphenyl phosphine oxide as raw materials, and the method has the advantages that operation is simple and convenient, catalyst cost is low, raw materials are stable, no pollution is caused, efficiency is high, and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of phosphorothioate compounds. Background technique [0002] Phosphorothioate is an important organophosphorus compound, which has a very wide range of applications in biology, medicine, pesticides and materials. In recent years, phosphorothioate pesticides have been widely used in agriculture, mainly as herbicides, insecticides and fungicides. The common phosphorothioate pesticides are: -Diisopropyl phosphorothioate, structural formula ) and omethoate (O, O dimethyl S-methylcarbamoyl phosphorothioate, structural formula )Wait. [0003] In the past, phosphorothioate compounds were mainly synthesized by the coupling reaction of P(O)-Cl compounds and nucleophiles (alcohols, phenols, etc.), and the reaction formula is as follows: [0004] [0005] In the formula, R 1 , R 2 Any one of alkyl, aryl, and alkoxy. It can be seen that the traditio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32
CPCC07F9/3229C07F9/3282
Inventor 张昌源郭火生邱云罗建徐舒婷王正平
Owner YICHUN UNIVERSITY