Method for preparing anethol trithione

A kind of technology of anetisol and phosphorus pentasulfide, which is applied in the field of preparation of anetisol, can solve the problems of low yield, difficult to control, high reaction temperature, etc., and achieve the effects of low reaction temperature, few by-products and mild reaction conditions

Active Publication Date: 2009-06-24
福建深纳生物工程有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The object of the present invention is to provide a kind of raw material that is easy to get and cheap, process is simple, easy to control for the problems such as high reaction temperature, uneasy control, and low yield in the existing method for synthesizing anetithion.

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  • Method for preparing anethol trithione
  • Method for preparing anethol trithione
  • Method for preparing anethol trithione

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) Add 48.0ml (0.4mol) of diethyl carbonate and toluene to a 500ml reaction flask, add 33.6g (0.3mol) of potassium tert-butoxide, raise the temperature to 80°C, and slowly add 15.0ml of p-methoxyacetophenone g (0.1mol) toluene solution. After adding, the reaction was completed for 4h. After the reaction was completed, it was lowered to room temperature, poured into water, and the organic layer was separated. The aqueous layer was extracted once with toluene, and the combined organic layers were washed with saturated NaCl solution. The organic layer was a toluene solution containing ethyl p-methoxybenzoyl acetate.

[0031] (2) 26.68g (0.12mol) of phosphorus pentasulfide, 4.8g (0.15mol) of sulfur, 106.5ml (0.5mol) of toluene and hexamethyldisiloxane were added to the reaction flask, and the mixture was heated to reflux. Slowly add the toluene solution of ethyl p-methoxybenzoylacetate prepared above dropwise, and the dropwise reaction is complete. The reaction solution ...

Embodiment 2

[0033] (1) Add 48.0ml (0.4mol) of diethyl carbonate and toluene to a 500ml reaction flask, add 22.4g (0.2mol) of potassium tert-butoxide, raise the temperature to 110°C, and slowly add 15.0ml of p-methoxyacetophenone g (0.1mol) toluene solution. The reaction was completed for 1 h. After the reaction was completed, it was lowered to room temperature, poured into water, and the organic layer was separated. The aqueous layer was extracted once with toluene, and the combined organic layers were washed with saturated NaCl solution. The organic layer was a toluene solution containing ethyl p-methoxybenzoyl acetate.

[0034] (2) Add 22.2 g (0.1 mol) of phosphorus pentasulfide, 4.8 g (0.15 mol) of sulfur, toluene, and 85.3 ml (0.4 mol) of hexamethyldisiloxane into the reaction flask, and heat the mixture to reflux. Slowly add the toluene solution of ethyl p-methoxybenzoylacetate prepared above dropwise, and the dropwise reaction is complete. The reaction solution was cooled, 35.6g o...

Embodiment 3

[0036] (1) Add toluene to the reaction bottle, slowly add 7.2g of sodium hydride (60% content) and 60.0ml (0.5mol) of diethyl carbonate under stirring, raise the temperature to 40 degrees, and slowly add p-methoxyphenyl ethyl Ketone 15.0g (0.1mol) toluene solution. After adding, the reaction was completed for 4h. After the reaction was completed, the reaction solution was poured into ice water, and the pH was adjusted to 9.0 with concentrated HCl. The aqueous layer was extracted with toluene, washed with sodium bicarbonate solution and saturated NaCl solution, and the organic layer was a toluene solution containing ethyl p-methoxybenzoyl acetate.

[0037] (2) Electric stirring 44.4g (0.2mol) of phosphorus pentasulfide, 3.2g (0.1mol) of sulfur, xylene, and 63.3ml (0.3mol) of hexamethyldisiloxane were added to a 500ml reaction flask, and the mixture was heated to reflux. Slowly add the toluene solution of ethyl p-methoxybenzoylacetate (about 0.1 mol) prepared above dropwise, a...

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Abstract

The invention discloses a preparation method of anethol trithione, relates to an organic compound, in particular to a method for preparing the anethol trithione by taking p-methoxy acetophenone and diethyl carbonate as raw materials to prepare p-methoxybenzoyl ethyl acetate under the action of alkali,and performing sulfur cyclization; and provides the preparation method of the anethol trithione with available and cheap raw materials, simple process, easy control, good product quality and high yield. The preparation method comprises the following steps: taking the p-methoxy acetophenone and the diethyl carbonate as the raw materials, and preparing a compound (I) ( the p-methoxybenzoyl ethyl acetate) by heating reaction under the action of the alkali; mixing the p-methoxybenzoyl ethyl acetate with phosphorus pentasulfide, sulfur, hexamethyldisiloxane and a solvent to obtain a mixture which is refluxed for reaction, and neutralized with potassium carbonate to obtain the product anethol trithione.

Description

technical field [0001] The present invention relates to an organic compound, in particular to a kind of ethyl p-methoxybenzoylacetate prepared by using p-methoxyacetophenone and diethyl carbonate as raw materials under the action of alkali, and then cyclized by sulfur Process for the preparation of anetis trisulfide. Background technique [0002] In 1947, anetis trithion was first synthesized by German Battcher and Luttringhaus, and in 1950, French scientists Halpem and Gaudin confirmed that anetis trithion has hepatoprotective and choleretic effects. Later, studies found that anetis trithione has the effect of promoting salivation and promoting digestion, and it was first used in the treatment of dry mouth in 1969. The latest research progress shows that anethione is very likely to become an effective drug for the treatment of lung cancer, and the National Institutes of Health of the United States have paid great attention to the relevant clinical trials. [0003] The sci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04A61P1/16
Inventor 马增欣朱少龙王亚璐游金龙卢文标
Owner 福建深纳生物工程有限公司
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