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Preparation method of triclabendazole sulfoxide

A technology of triclbendazole sulfoxide and triclbendazole, which is applied in the field of organic chemical synthesis, can solve the problems of high consumption, high price, large molecular weight and the like, and achieves the effect of safe operation

Inactive Publication Date: 2014-06-18
LIANYUNGANG YAHUI PHARMACHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And m-chloroperoxybenzoic acid market price is more expensive, and molecular weight is big, and consumption is many, and product is m-chlorobenzoic acid, can produce secondary pollution, therefore input raw material cost is bigger in preparation triclabendazole thionoxide, generally not for people choose

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 40g (0.11mol) of triclabendazole and 400ml of methanol into a 500ml reaction flask, stir and heat until the triclabendazole dissolves, the temperature drops to 20-25°C, and add 0.2g of vanadium pentoxide. Add 15.7g (0.138mol) of 30wt% hydrogen peroxide dropwise, the dropwise addition time is 30 minutes, the dropwise addition temperature is controlled at 20-25°C, and then keep warm at 20-25°C until crystallization occurs, then add 10.0g of sodium sulfite (0.080mol) , stirred for 30 minutes, added 100ml of water, cooled to 10-20°C, filtered to obtain the wet product triclabendazole sulfoxide.

[0023] Put the wet product triclabendazole sulfoxide into a 500ml reaction bottle, add 300ml acetone, heat to reflux, reflux for 30 minutes, cool down to 45~50°C and filter to remove the catalyst vanadium pentoxide. The filtrate was distilled to remove the solvent from acetone until white crystals precipitated, added 130ml of methanol, heated to reflux for 1 hour, cooled to 15~...

Embodiment 2

[0025] Add 20 g (0.055 mol) of triclobendazole and 200 ml of ethanol into a 500 ml reaction flask, stir and heat until the triclobendazole dissolves, cool down, and add 0.2 g of vanadium pentoxide. Add 7.3g (0.064mol) of 30% hydrogen peroxide dropwise, the dropwise addition time is 40 minutes, the dropwise addition temperature is controlled at 25-30°C, and then keep warm at 25-30°C until crystals are precipitated, then add 5.0g of sodium sulfite (0.040mol) , add 100ml of water, cool to 10~20°C and filter to obtain the wet product triclabendazole sulfoxide.

[0026] Put the wet product triclabendazole sulfoxide into a 500ml reaction bottle, add 300ml acetone, heat to reflux, reflux for 1h, cool down to 40-45°C and filter, distill acetone from the reaction solution, and stop the distillation when there is white material , add 65ml of methanol, heat up to reflux for 45 minutes, cool down to 15-25°C, filter, and dry at 90°C to obtain a dry weight of 14.2g of triclabendazole sulfon...

Embodiment 3

[0028] Add 20g (0.055mol) of triclabendazole and 200ml of formic acid into a 500ml reaction bottle, stir and heat until triclabendazole dissolves, cool down to 30-35°C, add 0.1g of vanadium pentoxide, drop 7.0g (0.07mol) of 30wt% hydrogen peroxide, the dropping time is 50 minutes, the dropping temperature is controlled at 30-35°C, and then kept at 30-35°C for 4 hours, add 5.0g of sodium sulfite (0.040mol), add 200ml water, cooled to 10-20°C and filtered to obtain the wet product triclabendazole sulfoxide.

[0029] Put the wet product triclabendazole sulfoxide into a 500ml reaction bottle, and add 300ml of acetone. Heat to reflux, reflux for 1h, cool down to 40-45°C and filter, distill acetone from the reaction solution, stop distillation when there is white material, add 65ml of 95% ethanol, heat up to reflux for 45 minutes, cool to 15-25°C and filter, 90°C Dried to obtain a dry weight of 12.9 g triclabendazole sulfoxide, HPLC purity 97.8%, of which 0.8% triclabendazole, 1.2%...

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PUM

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Abstract

The invention discloses a preparation method of triclabendazole sulfoxide. The preparation method comprises the following steps: carrying out an oxidizing reaction on triclabendazole and hydrogen peroxide in the presence of a solvent and a catalyst; and separating to obtain triclabendazole sulfoxide. By adopting a clean oxidizing agent hydrogen peroxide which is free from secondary pollution to oxidize, the preparation method has the characteristics of cleanness and environmental friendliness. The vanadium pentoxide catalyst is removed by filtration and is not left in the product. The reaction endpoint is judged by the reaction, and an excessive oxidizing agent is decomposed and removed through sodium sulfite, so that the preparation method is safe and reliable to operate.

Description

technical field [0001] The invention relates to a preparation method of triclabendazole sulfoxide, which belongs to the field of organic chemical synthesis. Background technique [0002] Triclobendazole sulfoxide is a derivative of triclodazole, which is metabolized and oxidized in animals to generate triclabendazole sulfoxide, thereby producing medicinal effects. Triclobendazole sulfoxide does not need to be oxidized in the body, and once absorbed after taking it, it will produce the drug effect immediately, with short preparation time, no side effects, high bioavailability, and is a new type of highly efficient anthelmintic drug. Its structure is as follows: [0003] . [0004] Use triclabendazole to prepare triclabendazole sulfoxide. At present, there are two oxidation methods, one is to use m-chloroperoxybenzoic acid as the oxidant, and the other is to use hydrogen peroxide as the oxidant. And m-chloroperoxybenzoic acid market price is more expensive, and molecular ...

Claims

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Application Information

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IPC IPC(8): C07D235/28
CPCC07D235/28
Inventor 张建峰张平虎李志陵朱云兵孙洋
Owner LIANYUNGANG YAHUI PHARMACHEM
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