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Method for preparing albendazole

A technology of albendazole and bromopropane, which is applied in the field of preparation of organic compounds, can solve problems such as inability to enter industrialized production, affect yield and quality, and restrict industrial production, and achieve the goal of eliminating potential safety hazards, low price, and easy purchase Effect

Active Publication Date: 2015-07-08
苏州诚和医药化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disadvantage of this method is that it uses highly poisonous chlorine gas, which brings serious safety hazards to production. At the same time, a large amount of by-product chlorides are produced in the synthesis process, which seriously affects its yield and quality. On the other hand, this method uses vulcanization Alkali is used as a reducing agent, and excess alkali sulfide reacts with bromopropane in the next step of propylation to produce thioether with a serious stench, which is difficult to handle and severely restricts industrial production. Therefore, this method cannot be used in industrial production at present.
In summary, there is an urgent need for a method to avoid the use of highly toxic drugs, while the quality and yield of intermediates are greatly improved, and no by-products that pollute the environment are produced, which is fully suitable for industrial production. This method has not been reported yet

Method used

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  • Method for preparing albendazole
  • Method for preparing albendazole

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Experimental program
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Effect test

Embodiment 1

[0023] Add 100 grams (0.52mol) of carbendazim (0.52mol), 49 grams (0.60mol) of sodium thiocyanate, and 500 grams of glacial acetic acid into a 1500ml reaction bottle. While stirring, control the temperature at 30-35°C, and slowly add hydrogen peroxide with a mass concentration of 28% 253g (2.08mol), keep the temperature at 30-35°C for 4 hours after the dropwise addition. After the heat preservation is over, vacuum distillation to recover glacial acetic acid. After the distillation of glacial acetic acid, add 500 grams of 20% potassium hydroxide aqueous solution (1.82mol) and 1.5 grams of benzyltriethylammonium chloride, adjust the temperature at 45-50 °C under stirring conditions, add 70.356 g (0.572 mol) of 1-bromopropane dropwise, after the addition is completed, slowly heat up to 55-60 °C, and at this temperature Keep warm for 6 hours, cool to room temperature and filter at the end of the heat preservation, wash with drinking water until neutral, drain, dissolve the material...

Embodiment 2

[0025] Add 109.6 grams (0.57mol) of carbendazim (0.57mol), 60.5 grams (0.74mol) of sodium thiocyanate, and 548 grams of glacial acetic acid into a 1500ml reaction bottle, and control the temperature at 30-35°C under stirring conditions, and slowly add hydrogen peroxide with a mass concentration of 28% 242 g (2.00 mol), keep the temperature at 30 to 35 °C for 4 hours after the dropwise addition. After the heat preservation is over, vacuum distillation to recover glacial acetic acid. After the distillation of glacial acetic acid, add 638 grams of 20% potassium hydroxide aqueous solution (2.28 mol) and 2.5 grams of benzyltriethylammonium chloride, adjust the temperature at 45-50 ° C under stirring conditions, add 91.143 g (0.741 mol) of 1-bromopropane dropwise, after the addition is complete, slowly raise the temperature to 55-60 ° C, and at this temperature Keep warm for 6 hours, cool to room temperature and filter at the end of the heat preservation, wash with drinking water unt...

Embodiment 3

[0027] Add 90 grams (0.47mol) of carbendazim (0.47mol), 56.7 grams (0.70mol) of sodium thiocyanate, and 450 grams of glacial acetic acid into a 1500ml reaction bottle, control the temperature at 30-35°C under stirring conditions, and slowly add hydrogen peroxide with a mass concentration of 28% 285 g (2.35 mol), keep the temperature at 30-35 °C for 4 hours after the dropwise addition, after the heat preservation is over, vacuum distillation to recover glacial acetic acid, after the distillation of glacial acetic acid, add 593 g of 20% potassium hydroxide aqueous solution (2.12 mol) 2.5 grams of benzyltriethylammonium chloride, adjust the temperature at 45-50 ° C under stirring conditions, add 69.372 g (0.564 mol) of 1-bromopropane dropwise, after the addition is complete, slowly heat up to 55-60 ° C, and at this temperature Keep warm for 6 hours, cool to room temperature and filter at the end of the heat preservation, wash with drinking water until neutral, drain, dissolve the ...

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Abstract

The invention relates to a method for preparing albendazole. The method comprises the following steps of: (a) adding carbendazim, sodium sulfocyanate and glacial acetic acid to a reactor, dropwise adding 28% hydrogen peroxide while controlling the temperature to be 25-40 DEG C, carrying out heat preservation and reaction for 4-6 hours after the dropwise adding process is completed, and obtaining thiocyanide after glacial acetic acid is recovered through negative-pressure distillation; and (b) adding 20% aqueous potassium hydroxide solution to the thiocyanide while adding benzyltriethylammonium chloride, then dropwise adding 1-bromopropane, and reacting for 4-8 hours while controlling the temperature to be 45-60 DEG C, thereby obtaining the albendazole. According to the method, the potential safety hazard caused by the fact that a highly toxic substance, namely chlorine gas, is used for preparing albendazole is avoided successfully, and the influence on the quality and yield of the product, caused by side reactions resulting from the adoption of the chlorine gas, is eliminated successfully, so that the quality and yield of an intermediate are improved greatly; meanwhile, the adoption of alkali sulfide is cancelled, and then, the environmental pollution caused by a byproduct, namely thioether, produced due to excessive alkali sulfide is avoided, so that the method is perfectly suitable for industrial production; and furthermore, all the raw materials are low in cost and are purchased easily, and the operation is safe.

Description

technical field [0001] The present invention relates to the preparation method of organic compound, specifically, it is a kind of method for preparing albendazole. Background technique [0002] Albendazole (Albendazole), molecular formula: C 12 h 15 N 3 o 2 S, molecular weight: 265.33, is a broad-spectrum, high-efficiency, and low-toxic insect repellent listed by Smith Kline Company in the United States. It is still widely used at home and abroad. It has a variety of synthesis methods, mainly o-nitroaniline method, o-phenylenediamine method, and carbendazim method. Among them, there are two carbendazim methods. Method 1: carbendazim is chlorosulfonated and iron powder reduced Repropylation, the disadvantage of this preparation process is the use of highly poisonous chlorosulfonic acid, and a large amount of waste acid and iron sludge are produced during the synthesis process, the production risk is high, and there is no effective treatment method for the three wastes wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/32
Inventor 王利明夏秋景陈洁
Owner 苏州诚和医药化学有限公司