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A preparing method of rafoxanide

A technology of iodoxanamide and chlorophenyl ether, which is applied in the field of preparation of iodoxanamide, can solve the problems of inconvenient industrial production, unsatisfactory yield, long reaction time, etc., and achieves easy operation, mild reaction and excellent reaction conditions. mild effect

Inactive Publication Date: 2016-04-06
ZHEJIANG ESIGMA BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method takes a long time to react, the yield of each step is not ideal, and it is not conducive to environmental protection, which brings inconvenience to industrial production

Method used

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  • A preparing method of rafoxanide

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Experimental program
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Effect test

Embodiment 1

[0025] The preparation of embodiment 1 iodoxanamide

[0026] (1) Preparation of 2-chloro-4-nitrophenyl-p-chlorophenyl ether

[0027] Add 25.71g (0.2mol) of p-chlorophenol and 77.13g of DMF to the reaction vessel, add 11.45g (0.204mol) of potassium hydroxide under stirring, react at 35°C for 20 minutes, and add 38.4g of 3,4-dichloronitrobenzene (0.2mol), catalyzer cuprous chloride 0.396g (0.004mol), be warming up to reflux temperature, react 5 hours, reaction solution is cooled to room temperature, filter and remove insoluble impurity, filtrate underpressure distillation reclaims solvent, add water 100ml stirring under room temperature, Ocher needle-like crystals were precipitated, filtered and dried to obtain 55.4 g of 2-chloro-4-nitrophenyl-p-chlorophenyl ether, with an HPLC purity of 98.52% and a yield of 96.1% (based on p-chlorophenol).

[0028] (2) Preparation of 4-amino-2-chlorophenyl-p-chlorophenyl ether

[0029] Add 28.4g (0.1mol) of 2-chloro-4-nitrophenyl-p-chlorophe...

Embodiment 2

[0034] Preparation of embodiment 22-chloro-4-nitrophenyl-p-chlorophenyl ether

[0035]Add 25.71g (0.2mol) of p-chlorophenol and 102.84g of DMF to the reaction vessel, add 11.76g (0.21mol) of potassium hydroxide under stirring, react at 38°C for 30 minutes, and add 38.4g of 3,4-dichloronitrobenzene (0.2mol), catalyzer cuprous chloride 0.594g (0.006mol), be warming up to reflux temperature, react 5.5 hours, reaction solution is cooled to room temperature, filter and remove insoluble impurity, filtrate underpressure distillation reclaims solvent, add water 100ml stirring under room temperature, Precipitated khaki needle-like crystals, filtered and dried to obtain 53.8 g of 2-chloro-4-nitrophenyl-p-chlorophenyl ether, with an HPLC purity of 97.34% and a yield of 92.2% (based on p-chlorophenol).

Embodiment 3

[0036] Preparation of Example 32-chloro-4-nitrophenyl-p-chlorophenyl ether

[0037] Add 25.71g (0.2mol) of p-chlorophenol and 128.55g of DMF into the reaction vessel, add 12.32g (0.22mol) of potassium hydroxide under stirring, react at 40°C for 40 minutes, and add 38.4g of 3,4-dichloronitrobenzene (0.2mol), catalyzer cuprous chloride 0.792g (0.008mol), be warming up to reflux temperature, react 6 hours, reaction solution is cooled to room temperature, filter and remove insoluble impurity, filtrate underpressure distillation reclaims solvent, add water 100ml and stir under room temperature, Ocher needle crystals were precipitated, filtered and dried to obtain 54.1 g of 2-chloro-4-nitrophenyl-p-chlorophenyl ether, with an HPLC purity of 97.80% and a yield of 93.67% (calculated as p-chlorophenol).

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Abstract

A preparing method of rafoxanide is provided. The method includes preparing 2-chloro-4-nitrophenyl tert-chlorophenyl ether by adopting p-chlorophenol and 3,4-dichloronitrobenzene as raw materials and adopting DMF as a solvent under catalysis of a catalyst that is cuprous chloride, preparing 4-amino-2-chlorophenyl tert-chlorophenyl ether by hydrogenating under catalysis of a 10% Pd / C catalyst, reacting 3,5-diiodosalicylic acid that is adopted as a raw material with an acyl chlorination reagent that is BTC / C2H4Cl2 to prepare 3,5-diiodosalicyloyl chloride, and subjecting the 4-amino-2-chlorophenyl tert-chlorophenyl ether and the 3,5-diiodosalicyloyl chloride to condensation to prepare the rafoxanide. The method is mild in reaction conditions, simple in process and easy in operation. A product of the method is high in purity and high in yield. The method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of iodoxanamide. Background technique [0002] Rafoxanide, also known as diiodoxanide, diiodoxanide, English name Rafoxanide, Chinese chemical name: 3-chloro-4-(p-chlorophenoxy)-3,5-di Iodine salicylanilide. Its structural formula is as follows: [0003] [0004] Iodothersanamide is a halogenated salicylanilide trematicide, off-white to brown powder, soluble in acetone, slightly soluble in chloroform or ethyl acetate, slightly soluble in methanol, insoluble in water. This product has the effect of resisting Fasciola hepatica, and can inhibit the phosphorylation process of the mitochondria of the parasite, thereby preventing the synthesis of adenosine triphosphate (ATP) in the parasite, resulting in the rapid weakening of the energy metabolism of the parasite and finally death. It has a strong affinity with blood proteins, so the d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C235/64
CPCC07C231/02C07C51/60C07C201/12C07C213/02C07C235/64C07C65/05C07C217/90C07C205/38
Inventor 吴中华张小朋陈贵才徐天华何奇雷闻鸣
Owner ZHEJIANG ESIGMA BIOTECH CO LTD
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