Method for preparing 5-(4- fluobenzene sulphonyloxy) benzimidazole-2-amido methyl formate

A technology of fluorobenzenesulfonyloxy and methyl carbamate, which is applied in the field of preparing 5-(4-fluorobenzenesulfonyloxy)benzimidazole-2-methyl carbamate, which can solve unfavorable industrial production and processing Problems such as cumbersome and high unit price of raw materials

Inactive Publication Date: 2007-05-23
CHANGZHOU YABANG QH PHARMACHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] But, the reaction yield of the method of U.S.Patent 4,639,463 report is low, and the selected 3-nitro-4-aminophenol, Raney nickel catalyst and ring-closing agent N, N-bis(

Method used

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  • Method for preparing 5-(4- fluobenzene sulphonyloxy) benzimidazole-2-amido methyl formate
  • Method for preparing 5-(4- fluobenzene sulphonyloxy) benzimidazole-2-amido methyl formate

Examples

Experimental program
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Embodiment 1

[0031] step 1

[0032] In a 150ml four-neck flask equipped with a stirring device and a thermometer, add 10.0g (0.092mol) of p-aminophenol and 10ml (0.120mol) of acetic anhydride in sequence, heat and stir, and reflux for 2 hours. The temperature continued to rise during the reaction. After the reaction was completed, the reaction solution was poured into a small amount of ice water, and crystals were precipitated. After suction filtration, the product was recrystallized with alcohol to obtain 13.2 g of paracetamol, with a yield of 94.9% and a melting point of 170°C.

[0033] step 2

[0034] In a 150ml four-necked flask equipped with a stirring device and a thermometer, add 80ml of 98% sulfuric acid, stir and cool down to below 10°C, add 9.4g (0.062mol) of paracetamol, cool to below 10°C, dropwise add 3.7ml98 % sulfuric acid and 3.8ml 96% nitric acid mixed acid solution, after adding, react for 2h. After the reaction stopped, under strong stirring, pour the reaction solutio...

Embodiment 2

[0036] Referring to the first reaction step of Example, first formylate and then nitrate to obtain 3-nitro-4-formylaminophenol.

Embodiment 3

[0038] Referring to the first reaction step of Example, propionylation and then nitration were carried out to obtain 3-nitro-4-propionylaminophenol.

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Abstract

The invention relates to a preparation method for 5-(4-fluorophenyl-sulfonyl)-benzimidazole-2-methyl carbamate. The method includes (1) using p-aminophenol as raw materials, and preparing a number of new 3-nitro-4-substituted aminophenol intermediates through acylation and denitrification; (2) carrying out a condensation reaction of 3-nitro-4-substituted aminophenol intermediates with the 4-fluorophenylsulfonyl chloride in the alkaline solution, and hydrolyzing to obtain 2-nitro-4-(4-fluorophenyl-sulfonyl)-aniline intermediates; (3) carrying out a reduction reaction of 2-nitro-4-(4-fluorophenyl-sulfonyl)-aniline intermediates to obtain 4-(4-fluorophenyl-sulfonyl)-o-phenylenediamine intermediates; and (4) carrying out a closed loop reaction of closed-loop agents and 4-(4-fluorophenyl-sulfonyl)-o-phenylenediamine to obtain 5-(4-fluorophenyl-sulfonyl)-benzimidazole-2-methyl carbamate. This invention has the advantages of high yield, small unit consumption, and low cost. The raw materials are cheap and the method is easy for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of 5-(4-fluorobenzenesulfonyloxy)benzimidazole-2-carbamate methyl ester, a benzimidazole anthelmintic chemical synthesis drug. Background technique [0002] Methyl 5-(4-fluorobenzenesulfonyloxy)benzimidazole-2-carbamate is a broad-spectrum anthelmintic that can be used both in humans and animals. It is also known as lubendazole, and its English name is luxabendazole. Benzimidazole chemical synthesis drug. [0003] The structural formula of 5-(4-fluorobenzenesulfonyloxy)benzimidazole-2-carbamate methyl ester is: [0004] [0005] At present, benzimidazole chemical synthetic drugs are widely used as broad-spectrum antiparasitic drugs, especially a class of efficient and safe anti-intestinal nematode drugs. The widespread use of such drugs has reduced the types and quantities of commonly used anti-parasitic drugs, shortened the course of treatment for anti-parasitic infections, and further simplified the ...

Claims

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Application Information

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IPC IPC(8): C07D235/32
Inventor 邱滔刘祥宜朱建民
Owner CHANGZHOU YABANG QH PHARMACHEM
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