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Preparation method of nifuratel

A technology of nifuratel and molar ratio, applied in the field of preparation of nifuratel, can solve the problems of low utilization rate of reaction raw materials, high cost of raw materials, high production cost, etc., shorten reaction time, reduce production cost, and reduce dosage Effect

Active Publication Date: 2022-05-13
YANCHENG KAILI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthetic routes of early nifuratel such as Belg pat.635608 (1963), CA61:16069c, and French patent Fr.M 4544 (1966), CA66:59221a, both take epichlorohydrin as starting material In the synthesis of nifuratel, methyl mercaptan or sodium methyl mercaptide was used in the reaction process. In order to improve the conversion rate of epichlorohydrin, excessive hydrazine hydrate is often used. The recent Chinese patent CN108084174B also reported the use of epichlorohydrin Propane is the route that starting material prepares nifuratel, and there is deficiency in such synthetic route: 1) methyl mercaptan or sodium methyl mercaptide taste foul smell, pollute environment, 2) metal sodium can be used in sodium methoxide / methanol system environment, There is a huge potential safety hazard, and it is very easy to cause combustion and explosion. 3) use excessive hydrazine hydrate to pollute the environment, excessive use, and high raw material cost; Nifuratel is synthesized with glycidyl methyl sulfide as the starting material, but calculated with glycidyl methyl sulfide, the yield of nifuratel is 65-70%, the yield is low, and the utilization rate of reaction raw materials is low , will increase the production cost

Method used

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  • Preparation method of nifuratel
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  • Preparation method of nifuratel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 prepares methylthiomethyl vinyl carbonate

[0034] The specific steps are as follows: Add 0.1mol glycidyl methyl sulfide to a 1L autoclave, add 0.002mol 1-hydroxyethyl-1,8-diazabicyclo[5.4.0]undec-7- Alkenyl bromide catalyst, sealed, and then continuously filled with carbon dioxide gas, and maintained within a certain pressure, heated to 85 ° C under microwave treatment with a power of 1000W for addition reaction, the reaction time is 5 hours, the reaction process is as follows figure 1 As shown in the reaction ①, put it in an ice bath and cool it down to 6°C. During the liquid reaction process, the body partly solidifies, releases excess carbon dioxide, and removes the liquid to obtain methylthiomethylethylene carbonate. Use ethanol at 2 to 6 °C, dried at 30-35 °C, and weighed. The results are shown in Table 1.

[0035] Table 1

[0036]

[0037]

[0038] It is found from the above table 1 that as the pressure increases, the amount of methylthiometh...

Embodiment 2

[0039] Embodiment 2 prepares methylthiomethyl vinyl carbonate

[0040] The specific steps are as follows: Add 0.1mol glycidyl methyl sulfide to a 1L autoclave, add 0.002mol 1-hydroxyethyl-1,8-diazabicyclo[5.4.0]undec-7- Alkenyl bromide catalyst, sealed, then continuously filled with carbon dioxide gas, and maintained within 1.6MPa, heated at a certain temperature under microwave treatment with a power of 1000W, and carried out an addition reaction. The reaction time is 5h. The reaction process is as follows figure 1As shown in the reaction ①, put it in an ice bath and cool it down to 6°C. During the liquid reaction process, the body partly solidifies, releases excess carbon dioxide, and removes the liquid to obtain methylthiomethylethylene carbonate. Use ethanol at 2 to 6 °C, dried at 30-35 °C, and weighed. The results are shown in Table 2.

[0041] Table 2

[0042]

[0043] Find through above table 2, the amount of glycidyl methyl sulfide is constant, and along with the ...

Embodiment 3

[0044] Embodiment 3 prepares methylthiomethyl vinyl carbonate

[0045] The specific steps are as follows: Add 0.1mol glycidyl methyl sulfide to a 1L autoclave, add 0.002mol 1-hydroxyethyl-1,8-diazabicyclo[5.4.0]undec-7- Alkenyl bromide catalyst, sealed, then continuously filled with carbon dioxide gas, and maintained within 1.7MPa, heated to 95°C under microwave treatment with a power of 1000W for addition reaction, the reaction time is a period of time, the reaction process is as follows figure 1 As shown in the reaction ①, put it in an ice bath and cool it down to 6°C. During the liquid reaction process, the body partly solidifies, releases excess carbon dioxide, and removes the liquid to obtain methylthiomethylethylene carbonate. Use ethanol at 2 to 6 °C, dried at 30-35 °C, and weighed. The results are shown in Table 3.

[0046] table 3

[0047]

[0048] Find through above table 3, the amount of glycidyl methyl sulfide is certain, and as time prolongs, the amount of th...

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Abstract

The invention discloses a preparation method of nifuratel, which comprises the following steps: taking epoxypropyl dimethyl sulfide as an initial raw material, carrying out a synthetic reaction with carbon dioxide to obtain methylthio methyl ethylene carbonate, then carrying out a synthetic reaction with tert-butyl carbazate to obtain N-(tert-butyl formate-amino)-5-methylthio methyl-2-oxazolidinone, and finally, carrying out a reaction on the N-(tert-butyl formate-amino)-5-methylthio methyl-2-oxazolidinone and the N-(tert-butyl formate-amino)-5-methylthio methyl-2-oxazolidinone to obtain the nifuratel. And carrying out condensation reaction with 5-nitrofurfural to obtain nifuratel. The nifuratel prepared by the method is relatively high in yield and purity, the preparation process is green and pollution-free, meanwhile, the problem of carbon dioxide waste gas pollution is solved, and the defects of environmental pollution, potential safety hazards, raw material waste and the like existing in an existing nifuratel synthesis process are overcome.

Description

technical field [0001] The invention relates to a preparation method of nifuratel, belonging to the technical field of pharmaceutical synthesis. Background technique [0002] Nifuratel, also known as furazolidone, has the molecular formula C 10 h 11 N 3 o 5 S, whose chemical name is 5-[(methylthio)methyl]-3-[(5-nitrofurfurylidene)amino]-2-oxazolidinone, is a kind of spectrum antibiotic, which can be used to treat bacteria, Vulva, vaginal infection, leucorrhea increase and urinary system infection caused by trichomonas, mold and candida, digestive tract amoebiasis and giardiasis. [0003] The synthetic routes of early nifuratel such as Belg pat.635608 (1963), CA61:16069c, and French patent Fr.M 4544 (1966), CA66:59221a, both take epichlorohydrin as starting material In the synthesis of nifuratel, methyl mercaptan or sodium methyl mercaptide was used in the reaction process. In order to improve the conversion rate of epichlorohydrin, excessive hydrazine hydrate is often u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D317/36
CPCC07D413/12C07D317/36Y02P20/141
Inventor 马向东黄伟杨毅跃
Owner YANCHENG KAILI PHARMA
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