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A kind of preparation new method of albendazole

A technology of albendazole and a new method, which is applied in the field of preparation of albendazole, can solve the problems of inability to industrialize production, high equipment investment cost, and high price of propanethiol, and achieve easy industrial production, low content of individual impurities, and safety risks low effect

Active Publication Date: 2021-01-08
CHANGZHOU YABANG QH PHARMACHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Chinese patent CN103172571B reports that m-dichlorobenzene is used as a starting material, and albendazole is prepared through nitration, amination, condensation, reduction, and ring closure reactions. In this route, propanethiol will be used in the condensation process, because propanethiol The price is high, and there is a pungent odor, it is difficult to meet the environmental protection requirements, and it cannot be industrialized
In addition, the hydrogenation reduction process used in this route is a high-risk process, which requires high equipment and automation control, and the investment cost of equipment is large.

Method used

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  • A kind of preparation new method of albendazole
  • A kind of preparation new method of albendazole
  • A kind of preparation new method of albendazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The preparation of step 1 2-nitro-5-propylthioaniline

[0049] In a 1L four-necked flask with a thermometer and a stirring device, start stirring, add 172.57g of 2-nitro-5-chloroaniline, ethanol 3 times the weight of 2-nitro-5-chloroaniline, and stir to heat up to 70 -78°C, add potassium sulfide aqueous solution dropwise with 1.2 times the molar weight, and continue to react for 4-5 hours after dropping, add iodo-n-propane with 1.2 times the molar weight of 2-nitro-5-chloroaniline, reflux for 2 hours, and react After cooling to 20°C, 203.14 g of dry product of 2-nitro-5-propylthioaniline was obtained by suction filtration, washing and drying, with a yield of 95.7% and an HPLC content of 98.4%. Mass spectrum data: [M]=213.15 (theoretical molecular weight 212.27)

[0050] Preparation of step 2 4-propylthio o-phenylenediamine

[0051] In a 1L four-necked flask with a thermometer and a stirring device, add ethanol that is 4 times the weight of 2-nitro-5-propylthioaniline,...

Embodiment 2

[0060] The preparation of step 1 2-nitro-5-propylthioaniline

[0061] In a 1L four-necked flask with a thermometer and a stirring device, start stirring, add 172.57g of 2-nitro-5-chloroaniline, methanol with 4 times the weight of 2-nitro-5-chloroaniline, stir and heat up to 60 -65°C, add 2.0 times the molar amount of sodium sulfide aqueous solution dropwise, continue the reaction for 4-5 hours after dropping, add brominated n-propane with 1.5 times the molar amount of 2-nitro-5-chloroaniline, reflux for 2 hours, and react After cooling to 20°C, 203.78 g of dry product of 2-nitro-5-propylthioaniline was obtained by suction filtration, washing and drying, with a yield of 96.0% and an HPLC content of 99.2%.

[0062] Preparation of step 2 4-propylthio o-phenylenediamine

[0063] In a 1L four-necked flask with a thermometer and a stirring device, add 2-nitro-5-propylthioaniline 5 times the weight of isopropanol, 106.14g of 2-nitro-5-propylthioaniline, 2 -Nitro-5-propylthioaniline...

Embodiment 3

[0072] Add 3000ml of reducing and stratified waste water and 30g of sulfur into a 5L reaction bottle, start stirring, raise the temperature to 90-100°C, keep stirring for 5 hours, add 12g of activated carbon, keep stirring at 80-90°C for 1 hour, suction filter, add 20g of chlorine to the filtrate manganese, turn on compressed air bubbling, control the temperature at 70-85°C until the lead acetate test paper is no longer black, filter with suction, concentrate the filtrate to a specific gravity of 1.58mg / ml, slowly cool down to 25°C, and filter with suction, the filter cake is 30- Air-dried at 40°C to obtain 385 g of white sodium thiosulfate with a titration content of 98.8%.

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Abstract

The invention provides a novel preparation method of albendazole. According to the invention, a novel synthetic route of albendazole is provided, wherein 2-nitro-5-chloroaniline is used as a startingmaterial and is subjected to reactions of substitution, condensation, reduction and cyclization to obtain high-purity albendazole. The method is characterized in that: the 2-nitro-5-chloroaniline is subjected to substituted reaction, and is subjected to condensation reaction with halogenated n-propane to obtain 2-nitro-5-albendazole aniline, which avoids the use of propanethiol with a high price and a stimulating odor. The use of a high-risk hydrogenation reduction process is avoided, a vulcanization alkali reduction process which is cheap and easily available in raw materials is used, a set of non-toxic treatment schemes for reducing layered waste water are provided, and meanwhile, secondary sodium thiosulfate can be obtained and the waste is turned into wealth. According to the method, the yield is high, the safety risk is low, the industrial production is facilitated, the content of the prepared albendazole is high, the content of single impurities is small, and the latest standardssuch as the US Pharmacopeia and the European Pharmacopoeia are met.

Description

technical field [0001] The invention belongs to the field of chemistry or medicinal chemistry, and in particular relates to a preparation method of albendazole. Background technique [0002] Albendazole (Albendazole), also known as albendazole, chemically named 5-propylthio-1H-benzimidazole-2-methyl carbamate, is a broad-spectrum high-efficiency and low-toxic anthelmintic drug, developed by SmithKline USA The company was listed for the first time in 1977. At present, the drug is widely used in the clinical treatment of various helminth infectious diseases. It has a strong killing effect on nematodes, trematodes, and tapeworms parasitic on humans and animals. It is effective on human cysticercosis and intestinal nematodes The effective rate is as high as 100%, and it can significantly inhibit the development of eggs, and has no accumulation in the body. [0003] Since the middle period of the 70s, there have been many reports about the synthetic route of albendazole both at ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/32
CPCC07D235/32
Inventor 朱建民苏文杰李志陵王学成
Owner CHANGZHOU YABANG QH PHARMACHEM
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