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Method for preparing 1H-imidazole-4-carbonitrile

A technology of imidazole and carbonitrile, which is applied in the field of preparation of 1H-imidazole-4-carbonitrile, can solve the problems of high price, unsuitability for industrial production, and difficult acquisition of raw materials, and achieve the advantages of convenient operation, low cost and high product purity Effect

Active Publication Date: 2019-02-15
DALIAN QIKAI MEDICAL TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0002] 1H-imidazole-4-carbonitrile is a very important pharmaceutical intermediate. So far, only US2009 / 101921234A discloses its preparation method: 4-imidazole formate, concentrated ammonia and ammonium chloride react to form 4-amidoimidazole , 4-amidoimidazole reacts with a cyanating agent to form 1H-imidazole-4-carbonitrile, but its raw materials are not easy to obtain and expensive, so it is not suitable for industrial production

Method used

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  • Method for preparing 1H-imidazole-4-carbonitrile

Examples

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Effect test

Embodiment 1

[0033] ①The preparation of 1H-imidazole-4-carbaldehyde, the steps are as follows:

[0034] In a 500ml four-necked flask, add 25.1g (0.254mol) 4-hydroxymethylimidazole and 125.5g methanol in sequence, the mass ratio of 4-hydroxymethylimidazole and methanol is 1:5, stir evenly, and add 66.3g (0.762mol) manganese dioxide, the molar ratio of 4-hydroxymethylimidazole and manganese dioxide is 1:3, after the feeding is completed, the temperature is raised to 70°C for 6 hours, then the reaction solution is cooled to 25°C, and the manganese mud is removed by filtration , the filtrate is 1H-imidazole-4-carbaldehyde reaction solution (0.229mol), the yield is 90%, and the next step is directly synthesized.

[0035] 2. The preparation of 4-methoxime imidazole, the steps are as follows:

[0036] Stir and cool down the 1H-imidazole-4-formaldehyde reaction liquid (0.229mol) obtained in step ① to 25°C, slowly add 19.1g (0.275mol) of hydroxylamine hydrochloride, the molar ratio of 1H-imidazole...

Embodiment 2

[0040] All the other steps are as follows with the preparation of embodiment 1,4-methoxyimidazole:

[0041] 2. The preparation of 4-methoxime imidazole, the steps are as follows:

[0042] Distill methanol under reduced pressure from step ① (0.229mol) 1H-imidazole-4-formaldehyde reaction solution, add 110g of pyridine, stir and cool down to 25°C, the mass ratio of 1H-imidazole-4-formaldehyde to pyridine is 1:5, slowly add hydrochloric acid Hydroxylamine 19.1g (0.275mol), the molar ratio of 1H-imidazole-4-carbaldehyde and hydroxylamine hydrochloride is 1:1.2, the temperature is controlled at 55°C, after the addition is completed, it is kept at room temperature for 2 hours, and the pyridine is distilled from the solvent to obtain a viscous kettle liquid 4-methoximylimidazole (0.227mol), yield 99%, directly synthesized to the next step.

Embodiment 3

[0044] ①The preparation of 1H-imidazole-4-carbaldehyde, the steps are as follows:

[0045]In a 500ml four-necked flask, add 25.1g (0.254mol) 4-hydroxymethylimidazole and 125.5g methanol in sequence, the mass ratio of 4-hydroxymethylimidazole and methanol is 1:5, stir evenly, and add 123.7g (1.422mol) manganese dioxide, the molar ratio of 4-hydroxymethylimidazole and manganese dioxide is 1:5.6, after the addition is completed, the temperature is raised to 40°C for 6 hours, then the reaction solution is cooled to 25°C, and the manganese mud is removed by filtration , the filtrate is 1H-imidazole-4-carbaldehyde reaction liquid (0.229mol), the yield is 92%, and the next step is directly synthesized.

[0046] All the other steps are the same as in Example 1.

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Abstract

The invention discloses a method for preparing 1H-imidazole-4-carbonitrile, and particularly relates to the technical field of fine chemical product preparation. The method for preparing 1H-imidazole-4-carbonitrile comprises the following steps: step (1) oxidation reaction: performing oxidation on 4-hydroxymethylimidazole to obtain 1H-imidazole-4-carboxaldehyde; step (2) oximation reaction: performing oximation reaction on the 1H-imidazole-4-carboxaldehyde prepared in the step (1) to obtain 4-formaldoximido imidazole; and step (3) dehydration reaction: performing dehydration reaction on the 4-formaldoximido imidazole prepared in the step (2) to obtain 1H-imidazole-4-carbonitrile. The method provided by the invention has the advantages of reducing many steps due to intermediates are not purified from the beginning of the reaction to the end of the process, reducing energy consumption due to high and low temperature equipment is not used, reducing environmental pollution due to acidic wastewater is not generated, and having a high yield of products; the invention proposes a complete process route for synthesizing 1H-imidazole-4-carbonitrile by using 4-hydroxymethylimidazole as a rawmaterial; and the method is simple in process and easy to realize industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of fine chemical products, and in particular relates to a preparation method of 1H-imidazole-4-carbonitrile. Background technique [0002] 1H-imidazole-4-carbonitrile is a very important pharmaceutical intermediate. So far, only US2009 / 101921234A discloses its preparation method: 4-imidazole formate, concentrated ammonia and ammonium chloride react to form 4-amidoimidazole , 4-amidoimidazole reacts with a cyanating agent to form 1H-imidazole-4-carbonitrile, but its raw materials are not easy to obtain and expensive, so it is not suitable for industrial production. In order to meet market demand, our company researches and develops a preparation method of 1H-imidazole-4-carbonitrile with easy-to-obtain raw materials, simple industrialization process and low cost. Contents of the invention [0003] The purpose of the present invention is to provide a kind of raw material is easy to get, and industriali...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/90C07D233/64
CPCC07D233/64C07D233/90
Inventor 韩晓东张洪学姜殿平
Owner DALIAN QIKAI MEDICAL TECH
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