Albendazole synthesis method

A technology of albendazole and a synthesis method, which is applied to the synthesis field of veterinary drugs and pharmaceutical raw material albendazole, can solve the problems of high total yield, multiple yields and the like, and achieves high total yield, clean raw materials and no pollution , the effect of good industrialization prospects

Inactive Publication Date: 2019-03-01
SHANDONG GUOBANG PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method solves the defect that there are many impurities and low yield in the current production process. The addition reaction of propylene is introduced, the raw material is clean and pollution-free, and the introduction of highly toxic sodium cyanide is avoided. The total yield is high and has a good industrialization prospect.

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment one: One of the preparations of thiocyanate chloride (SCNCl)

[0038] Take 7.60 g (0.10 mol) of ammonium thiocyanate and add it to a four-necked flask with mechanical stirring, add 76.00 ml of methanol, cool and control the temperature to -10°C, and slowly introduce 7.10 g (0.10 mol) of chlorine gas under stirring, and the introduction is complete Continue the insulation reaction for 30 minutes, then filter out the precipitated ammonium chloride, and the filtrate is for subsequent use, wherein the filtrate contains 8.92 grams of thiocyanate chloride (SCNCl), and the yield is 95.37%.

Embodiment 2

[0039] Embodiment two: Chlorothiocyanate (SCNCl) preparation two

[0040] Take 7.60 g (0.10 mol) of ammonium thiocyanate and add it to a four-neck flask with mechanical stirring, add 76.00 ml of methanol, cool and control the temperature to -10°C, and slowly introduce 7.81 g (0.11 mol) of chlorine gas under stirring, and the introduction is complete Continue the insulation reaction for 30 minutes, then filter out the precipitated ammonium chloride, and the filtrate is for subsequent use, wherein the filtrate contains 9.26 grams of chlorothiocyanate (SCNCl), and the yield is 99.02%.

Embodiment 3

[0041] Embodiment three: Thiocyanine Chloride (SCNCl) Preparation Three

[0042]Take 7.60 g (0.10 mol) of ammonium thiocyanate and add it to a four-neck flask with mechanical stirring, add 76.00 ml of methanol, cool and control the temperature to -10°C, and slowly introduce 9.23 g (0.13 mol) of chlorine gas under stirring, and the introduction is complete Continue the insulation reaction for 30 minutes, then filter out the precipitated ammonium chloride, and the filtrate is for subsequent use, wherein the filtrate contains 9.24 grams of thiocyanate chloride (SCNCl), and the yield is 98.78%.

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Abstract

The invention discloses an albendazole synthesis method. The albendazole synthesis method includes reacting ammonium thiocyanate with chlorine gas in a lower alcohol solvent to obtain chlorothiocyanate, reacting ortho-nitroaniline with the chlorothiocyanate in the lower alcohol solvent to obtain 4-thiocyano-2-nitroaniline, reacting the 4-thiocyano-2-nitroaniline with a sodium hydroxide solution toobtain 4-sodium sulfonate-2-nitroaniline, performing hydrochloric acid acidification to obtain 4-mercapto-2-nitroaniline, subjecting the 4-mercapto-2-nitroaniline and propylene to Markovnikov addition reaction to obtain 4-propylthio-2-nitroaniline, and reacting 4-propylthio-o-phenylenediamine with methylcyanocarbamate to obtain albendazole. The albendazole synthesis method has the advantages thata novel synthetic route is applied to prepare the albendazole, the defects of high impurity quantity and low yield in the current production process are overcome, the chlorothiocyanate is prepared toserve as an intermediate and then reacts with the ortho-nitroaniline, and impurities can be avoided effectively; the propylene is introduced for the addition reaction, raw materials are clean and free from pollution, introduction of highly toxic sodium cyanide is avoided, the total yield is high, and the albendazole synthesis method has a good industrialization prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemical production, in particular to a method for synthesizing albendazole, a veterinary drug and a pharmaceutical raw material drug. Background technique [0002] Albendazole is also known as albendazole, albendazole, albendazole, prothiocarbendazim, anti-dermamine, Changchongqing, etc., chemical name 5-propylthio-benzimidazole-2-carbamate methyl ester, molecular formula C 12 h 15 N 3 o 2 S, relative molecular weight 265.33, CAS No. 54965-21-8. White to pale yellow crystalline powder, odorless, melting point 208-210°C, insoluble in water, slightly soluble in hot dilute hydrochloric acid, acetone or chloroform, soluble in methanol, ethanol or acetic acid. Its structural formula is: [0003] [0004] Albendazole was developed by Smith Kline Bichem Company (predecessor of GlaxoSmithKline). It is a broad-spectrum thiabendazole anthelmintic drug, which can be used for humans and animals, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/32
CPCC07D235/32
Inventor 王友杰刘聪乔建超
Owner SHANDONG GUOBANG PHARMA
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