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Synthesis method of (R,S)-S-secondary butyl o-ethyl-2-oxo-1,3-thiazolidine-3-thiosulphate

A technology for the synthesis of ethylphosphorothioate and its application in (R,S)-S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylthio In the field of phosphate ester synthesis, it can solve the problems of low intermediate content, affecting product content, complex synthesis process, etc., and achieve the effects of high yield, simple operation and simple process

Inactive Publication Date: 2006-03-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The substance is a light yellow oily liquid with a boiling point of 85-86°C / 1mmHg. It is lively and easy to decompose, and the synthesis process is complex, resulting in low content of this intermediate, which further affects the content of the product.

Method used

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  • Synthesis method of (R,S)-S-secondary butyl o-ethyl-2-oxo-1,3-thiazolidine-3-thiosulphate
  • Synthesis method of (R,S)-S-secondary butyl o-ethyl-2-oxo-1,3-thiazolidine-3-thiosulphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 500 mL four-necked flask, add 31-2 g (0.3 mol) 2-thiazolidinone, 42.2 mL (0.3 mol) triethylamine and 200 mL toluene, and stir with electric power. Heat to 100°C, and add 67.5mL (0.42mol) O,O'-diethylthiophosphoryl chloride dropwise. After the dripping is completed, the heat preservation reaction is continued for 4 hours. After the reaction is complete, cool to room temperature, wash with water, dry the toluene layer with anhydrous sodium sulfate, filter, and desolvate to obtain brown-yellow O,O'-diethyl-2-oxo-1,3-thiazolidine-3-yl Thiophosphate.

[0023] Add the above-mentioned O, O'-diethyl-2-oxo-1,3-thiazolidine-3-ylthiophosphate (in 0.276 mol) and 82.5 mL (0.55 mol) 33 into a 250 mL four-necked flask. % Dimethylamine aqueous solution, stir, heat to reflux, keep the temperature and react for 20 hours. The reaction was stopped, and the reaction solution was concentrated to obtain a pale yellow viscous phosphorothioate ammonium salt. The above-mentioned phosphorothioat...

Embodiment 2

[0029] In a 500 mL four-necked flask, 31.2 g (0.3 mol) of 2-thiazolidinone, 27.2 mL (0.33 mol) of pyridine and 200 mL of toluene were added, and stirred with electric power. Heat to 90°C, and add 57.9 mL (0.36 mol) O,O'-diethylthiophosphoryl chloride dropwise. After the dripping is completed, the heat preservation reaction is continued for 7 hours. After the reaction is complete, cool to room temperature, wash with water, dry the toluene layer with anhydrous sodium sulfate, filter, and desolvate to obtain brown-yellow O,O'-diethyl-2-oxo-1,3-thiazolidine-3-yl Thiophosphate.

[0030] Add the above-mentioned O, O'-diethyl-2-oxo-1,3-thiazolidine-3-ylthiophosphate (0.273mol) and 182mL (0.82mol) 33% into a 250mL four-necked flask The diethylamine aqueous solution was stirred, heated to reflux, and the reaction was kept for 30 hours. The reaction was stopped and concentrated to obtain a pale yellow viscous phosphorothioate ammonium salt. The above-mentioned phosphorothioate ammonium salt...

Embodiment 3

[0032] In a 500 mL four-necked flask, 31.2 g (0.3 mol) 2-thiazolidinone, 40.3 g (0.33 mol) 4-dimethylaminopyridine and 200 mL xylene were added, and stirred with electric power. Heat to 90°C, and add 57.9 mL (0.36 mol) O,O'-diethylthiophosphoryl chloride dropwise. After the dripping is completed, the heat preservation reaction is continued for 7 hours. After the reaction is complete, cool to room temperature, wash with water, dry the toluene layer with anhydrous sodium sulfate, filter, and desolvate to obtain brown-yellow O,O'-diethyl-2-oxo-1,3-thiazolidine-3-yl Thiophosphate.

[0033] Add the above-mentioned O, O'-diethyl-2-oxo-1,3-thiazolidine-3-yl thiophosphate (in 0.273 mol) and 82.5 mL (0.55 mol) 33 into a 250 mL four-necked flask. % Dimethylamine aqueous solution, stir, heat to reflux, keep the temperature for 30 hours and react. The reaction was stopped and concentrated to obtain a pale yellow viscous phosphorothioate ammonium salt. The above-mentioned phosphorothioate ammo...

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Abstract

A process for preparing (R, S)-S-parabutyl-O-ethyl-2-oxy-1, 3-thiazolidine-3-yl thiophosphate includes such steps as reaction between 2-thiazolidinone and O, O'-diethyl thiophosphoryl chloride in arylhydrocarbon under the action of organic alkali to obtain O, O'-diethyl-2-oxy-1,3-thiazolidine-3-yl thionphosphate, reflux reaction on the aqueous solution of excessive lipoamine to obtain ammonium thiophosphate, reflux reaction on bromoparabutane in arylhydrocarbon-water system, and post-treating.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing (R, S)-S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidine-3-yl phosphorothioate. (2) Background technology [0002] (R,S)-S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidine-3-yl phosphorothioate, namely thiazophos, common name: fosthiazate, is a Japanese company from Ishihara A novel, highly effective, and broad-spectrum non-fumigation type organophosphorus insecticide and nematicide was developed. Research results show that thiazophos has a systemic transport effect in plants, has broad-spectrum activity on plant parasitic nematodes and pests, and is an ideal agent for preventing and controlling plant parasitic nematodes. [0003] Regarding the synthesis of (R, S)-S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidine-3-yl phosphorothioate, the methods reported in the literature are all based on 2- Thiazolidinone and O-ethyl-S-sec-butyl thiophosphoryl chloride as raw materials are obtained by condensation reaction in the presence...

Claims

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Application Information

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IPC IPC(8): C07F9/165
Inventor 翁建全沈德隆谭成侠
Owner ZHEJIANG UNIV OF TECH
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