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Preparation method of 4-nitroimidazole and 4,5-dimetridazloe

A technology of dinitroimidazole and nitroimidazole is applied in chemical recycling, organic chemistry and other directions to achieve the effect of improving synthesis efficiency and easy separation

Inactive Publication Date: 2015-09-09
ZHONGBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It must be pointed out that the electron cloud distribution of the nitrogen-containing imidazole ring is completely different from that of the benzene ring, so the nitration of imidazole is more difficult than that of the benzene ring, although SO 4 2- / ZrO 2 Superacids have better performance in the nitration of aromatic hydrocarbons, but there is no literature mentioning the use of SO 4 2- / ZrO 2 Nitration of imidazoles catalyzed by superacids

Method used

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  • Preparation method of 4-nitroimidazole and 4,5-dimetridazloe

Examples

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Effect test

example 1

[0021] Example 1: A kind of synthetic method of 4-nitroimidazole

[0022] Step 1. In a polytetrafluoroethylene-lined stainless steel reactor, the N 2 o 5 Dissolves in fuming nitric acid to form N 2 o 5 / fuming nitric acid saturated solution, followed by adding mesoporous SO 4 2- / ZrO 2 -CeO 2 The superacid catalyst and imidazole are stirred and mixed at room temperature to form a slurry reaction liquid, wherein the molar ratio of imidazole to fuming nitric acid is 1 / 2, and the amount of catalyst is 10% of the mass of fuming nitric acid;

[0023] Step 2. Seal the reaction kettle tightly, raise the temperature to 25°C, and stir until the reaction is complete;

[0024] Step 3, cooling and diluting the reaction solution in step 2 in ice water, standing, layering, and filtering to recover the catalyst, extracting and filtering the reaction solution with dichloromethane, taking the organic phase, rotary evaporation, and drying to obtain 4-nitroimidazole , the yield is 72%, ...

example 2

[0025] Example 2: A kind of synthetic method of 4-nitroimidazole

[0026] Step 1. In a polytetrafluoroethylene-lined stainless steel reactor, the N 2 o 5 Dissolves in fuming nitric acid to form N 2 o 5 / fuming nitric acid saturated solution, followed by adding mesoporous SO 4 2- / ZrO 2 -CeO 2 The superacid catalyst and imidazole are stirred and mixed at room temperature to form a slurry reaction liquid, wherein the molar ratio of imidazole to fuming nitric acid is 1 / 3, and the amount of catalyst used is 10% of the mass of fuming nitric acid.

[0027] Step 2. Seal the reaction kettle tightly, raise the temperature to 30°C, and stir until the reaction is complete;

[0028] Step 3, cooling and diluting the reaction solution in step 2 in ice water, standing, layering, and filtering to recover the catalyst, extracting and filtering the reaction solution with dichloromethane, taking the organic phase, rotary evaporation, and drying to obtain 4-nitroimidazole , the yield is ...

example 3

[0029] Example 3: A kind of synthetic method of 4-nitroimidazole

[0030] Step 1. In a polytetrafluoroethylene-lined stainless steel reactor, the N 2 o 5 Dissolves in fuming nitric acid to form N 2 o 5 / fuming nitric acid saturated solution, followed by adding mesoporous SO 4 2- / ZrO 2 -CeO 2 The superacid catalyst and imidazole are stirred and mixed at room temperature to form a slurry reaction liquid, wherein the molar ratio of imidazole to fuming nitric acid is 1 / 4, and the amount of catalyst used is 15% of the mass of fuming nitric acid.

[0031] Step 2. Seal the reactor, heat up to 50°C, and stir until the reaction is complete;

[0032] Step 3, cooling and diluting the reaction solution in step 2 in ice water, standing, layering, and filtering to recover the catalyst, extracting and filtering the reaction solution with dichloromethane, taking the organic phase, rotary evaporation, and drying to obtain 4-nitroimidazole , the yield is 90%, the purity is 95%, the me...

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Abstract

The invention relates to a preparation method of 4-nitroimidazole and 4,5-dimetridazloe, and in particular relates to a method for catalyzing a nitroimidazole compound by mesoporous SO4<2-> / ZrO2-CeO2 super acid. According to the method, a N2O5 / nitrosonitric acid saturated solution serves as a nitrating agent and super acid serves as a catalyst; imidazole and 4-nitroimidazole are added respectively; a reaction kettle is sealed after slurry reaction liquid is formed by stirring and mixing at normal temperature; reaction is performed respectively at the temperature of 25-50 DEG C and 110-130 DEG C until the raw materials are transformed completely; and the productive rates of 4-nitroimidazole and 4,5-dimetridazloe are 72-90% and 66-85% respectively. Compared with the existing literature, the method provided by the invention has the advantages of avoiding usage of mixed acid such as sulfuric acid and anhydride and improving the synthesis efficiency of the nitrating agent; and the product is easy to separate and the catalyst can be recycled, so that the method is an environmental-friendly green imidazole nitration process.

Description

technical field [0001] The invention relates to a preparation method of 4-nitroimidazole and 4,5-dinitroimidazole, in particular to a mesoporous SO 4 2- / ZrO 2 -CeO 2 A method for superacid catalyzed nitration of imidazole compounds. Background technique [0002] Nitroimidazole compounds are a new class of energetically insensitive explosives, and are also important intermediates in the synthesis of antifungal drugs, cardiovascular drugs and anticancer drugs. Among them, 4-nitroimidazole, 4,5-dinitro The study of imidazole is of particular concern. S. Bulusu and J. R. Cho et al. (S. Bulusu, R. Damavarapu, J.R. Autera, et al. J. Phys. Chem., 1995, 99: 5009-5015.; J.R. Cho, K.J. Kim, S.G. Cho, et al . J. Heterocyclic Chem., 2001, 38: 141-147.) 70% nitric acid and oleum were made into mixed acid nitrating agent respectively, reacted at 125°C for 8h, and imidazole was directly nitrated to obtain 4-nitroimidazole, the yield The highest is only 46%; Zhao Deming et al. (Zhao...

Claims

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Application Information

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IPC IPC(8): C07D233/92C07D233/91B01J27/053
CPCY02P20/584C07D233/92B01J27/053C07D233/91
Inventor 梁栋李永祥王建龙姜振民李志华
Owner ZHONGBEI UNIV
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