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Green synthesis method of prop-2-yn-1-yl benzenesulfonate

A green synthesis, propargyl ester technology, applied in the preparation of pesticide intermediates, the pharmaceutical field, can solve the problems of easy polymerization and volatilization, high reactivity, difficult to improve product purity, etc., to achieve mild reaction conditions, high yield, operation Simple and convenient effect

Inactive Publication Date: 2019-03-12
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reactivity of propargyl chloride and propargyl bromide is high, and propargyl can be quickly introduced on the corresponding functional group; but there are many shortcomings: due to the high reactivity, it is easy to introduce multiple propargyl; propargyl Chlorine and propargyl bromide are easy to polymerize and volatilize, and are highly toxic. Generally, they must be prepared as toluene solution for storage and use.
[0005] At present, most of the reported synthesis methods of propargyl benzenesulfonate are to dissolve benzenesulfonyl chloride and propargyl alcohol in an organic solvent, and use triethylamine or pyridine as a base to catalyze the reaction (CN107840812A). This process has a high cost. It is necessary to remove triethylamine or pyridine so that the operation is complicated, and the generated propargyl benzenesulfonate is easy to react with triethylamine or pyridine to produce quaternary ammonium base, which leads to the difficulty of post-processing after the increase of impurities, and it is difficult to improve the purity of the product

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0026] Add 5 kg of benzenesulfonyl chloride, 1.9 kg of propargyl alcohol and 5 kg of water into a 50-liter reactor, turn on the cooling device, control the temperature at 15°C, and add 3 kg of sodium carbonate / 10 kg of aqueous solution dropwise within 2 hours; Stir the reaction at 15°C, the reaction of benzenesulfonyl chloride in the gas phase detection system is complete, static liquid separation, the organic phase is washed with 2 × 5 kg of salt water, dried over anhydrous sodium sulfate, and distilled under reduced pressure to collect 142-148°C / 4mmHg fractions, 3.8 kg of propargyl benzenesulfonate was obtained with a yield of 69% and a gas phase purity of 99.1%.

Embodiment 2

[0028] Add 5 kg of potassium carbonate and 20 kg of water into a 50-liter reactor, stir to dissolve and add 1.9 kg of propargyl alcohol, turn on the cooling device, control the temperature at 10°C, and add 5 kg of benzenesulfonyl chloride dropwise within 2 hours; the dropwise addition is completed , continue to stir the reaction at 10°C, the reaction of benzenesulfonyl chloride in the gas phase detection system is complete, static separation, the organic phase is washed with 2 × 5 kg of salt water, dried over anhydrous sodium sulfate, distilled under reduced pressure, and collected at 142-148°C / 4mmHg Distillate, obtain 4.2 kilograms of propargyl benzenesulfonates, yield 76%, gas phase purity 99.4%.

Embodiment 3

[0030] Add 5 kg of benzenesulfonyl chloride, 2 kg of propargyl alcohol and 10 kg of water into a 50-liter reactor, turn on the cooling device, control the temperature at -5°C, and add 12 kg of 10% sodium hydroxide aqueous solution dropwise within 2 hours; Continue to stir the reaction at -5°C, the reaction of benzenesulfonyl chloride in the gas phase detection system is complete, static separation, the organic phase is washed with 2 × 5 kg of salt water, dried over anhydrous sodium sulfate, distilled under reduced pressure, and collected at 142-148°C / 4mmHg Distillate, obtain 4.8 kilograms of propargyl benzenesulfonates, yield 87%, gas phase purity 99.6%.

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Abstract

The invention discloses a green synthesis method of prop-2-yn-1-yl benzenesulfonate. The method is characterized in that benzene sulfonyl chloride and propargyl alcohol are taken as raw materials, a reaction is promoted by taking inorganic base as an acid capture agent in an aqueous phase, so as to obtain a high-purity target product; the method has the advantages that the related reaction conditions are mild, the yield is high, operation is simple and convenient, the green and environmental protection effects are realized, and large-scale production is promoted.

Description

technical field [0001] The invention relates to the technical field of preparation of medicine and pesticide intermediates, in particular to a green synthesis method of propargyl benzenesulfonate. Background technique [0002] The propargyl structure is an important group of some medicines. For example, rasagiline, an important drug for the treatment of primary Parkinson's disease, needs to introduce a propargyl segment; similarly, it is used to process mosquito coils, electric mosquito coils, liquid mosquito coils and sprays Proparethrin, which is used to control domestic pests such as houseflies, mosquitoes, lice, and cockroaches, must also have a propargyl moiety in its structure. In the existing methods for introducing propargyl moieties, propargyl halides are mostly used, such as propargyl chloride and propargyl bromide. The reactivity of propargyl chloride and propargyl bromide is high, and propargyl can be quickly introduced on the corresponding functional group; but...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/73C07C303/28C07C303/44
CPCC07C303/28C07C303/44C07C309/73
Inventor 刘明荣陆军刘辉吴志民许佳
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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