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Synthesis method of 4(5)-hydroxymethylimidazole

A technology for the synthesis of hydroxymethylimidazole and its synthesis method, which is applied in the field of synthesis of 4-hydroxymethylimidazole, can solve problems such as excessive generation of industrial waste liquid, unfavorable industrialization promotion, and unsatisfactory yield, and achieve high industrial promotion value, Strong selectivity and effect of increasing concentration

Active Publication Date: 2016-06-01
ITIC MEDCHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The total yield of the method is 49.6%, which is the closest to the prior art of the present invention. The invention uses 4,5-dicarboxylic acid imidazole as a raw material to carry out relatively in-depth exploration and research on the reaction process, and has carried out a relatively large process Improvement, better process conditions have been achieved, but the raw materials are expensive, too much industrial waste liquid is produced, the operation is more complicated and the yield is not ideal, which is not conducive to the promotion of industrialization

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  • Synthesis method of 4(5)-hydroxymethylimidazole
  • Synthesis method of 4(5)-hydroxymethylimidazole
  • Synthesis method of 4(5)-hydroxymethylimidazole

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preparation example Construction

[0063] Loaded Ni-Cu / SiO 2 The preparation method of catalyst comprises the following steps:

[0064] The copper nitrate of 1.268g and the nickel nitrate of 1.652g were dissolved in 10mL deionized water, and then the solution obtained was added dropwise to 3gSi0 2 and stir rapidly with a glass rod, place the resulting mixture in the air for 12h, put it into a 120°C oven and heat it for 12h, and then roast it at 500°C for 3h to obtain a catalyst precursor. Hydrogen is produced after reduction at 350°C for 1h.

[0065] Add load Ni-Cu / SiO 2 The catalyst can effectively catalyze the reduction of 4(5)-imidazole ethyl carboxylate to obtain 4(5)-hydroxymethylimidazole, with the support of Ni-Cu / SiO 2 With the increase of the amount of catalyst added, the corresponding product yield is also improved. According to the experimental data, the present invention adopts the supported Ni-Cu / SiO 2 The catalyst addition mass is 8-12g, wherein when the addition mass is 10g, the yield is the hi...

Embodiment 1

[0067] A kind of synthetic method of 4(5)-hydroxymethylimidazole, comprises the following operation steps:

[0068] The first step: decarboxylation reaction:

[0069] Mix 40g of 4,5-dicarboxylic imidazole, 1200mL of acetic anhydride, and 5g of manganese dioxide solid under reflux for 8 hours, filter and concentrate the filtrate to dryness.

[0070] Add 600 mL of 50% ethanol aqueous solution to the obtained solid and heat to reflux for 2 hours. After heating to reflux, filter while it is hot and add 10 g of solid sodium nitrate to the filtrate, stir well, let it cool naturally overnight, and filter again after overnight to obtain solid 4(5)-carboxylic acid imidazole;

[0071] The second step: esterification reaction:

[0072] Mix 50g of 4(5)-imidazole carboxylate, 1000mL of ethanol, 30mL of concentrated sulfuric acid and 10g of ferric sulfate powder and heat to reflux for 2h. After the reflux reaction, cool to room temperature and add 5% NaOH aqueous solution dropwise to adju...

Embodiment 2

[0076] A kind of synthetic method of 4(5)-hydroxymethylimidazole, comprises the following operation steps:

[0077] The first step: decarboxylation reaction:

[0078] Mix 40g of 4,5-dicarboxylic imidazole, 1200mL of acetic anhydride, and 6g of manganese dioxide solids, heat to reflux for 8h, filter and concentrate the filtrate to dryness,

[0079] Add 600 mL of 50% ethanol aqueous solution to the obtained solid and heat to reflux for 2 hours. After heating to reflux, filter while it is hot and add 8 g of solid sodium nitrate to the filtrate, stir evenly, let it cool naturally overnight, and filter again after overnight to obtain solid 4(5)-carboxylic acid imidazole;

[0080] The second step: esterification reaction:

[0081] 50g of 4(5)-carboxylic acid imidazole, 1000mL of ethanol, 30mL of concentrated sulfuric acid and 10.5g of iron sulfate powder were mixed and heated to reflux for 2h. Concentrate under pressure to dryness to obtain mixed solids, add 30mL of water to refl...

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Abstract

The invention discloses a synthesis method of 4(5)-hydroxymethylimidazole. With 4,5-imidazoledicarboxylic acid as the raw material, decarboxylic reaction, esterification reaction and reduction reaction are conducted, manganese dioxide solid, ferric sulfate powder and a loaded Ni-Cu / SiO2 catalyst are added for catalytic reaction, reaction efficiency is improved, and reaction operation is simplified; meanwhile, the reaction process is improved, that is, the precipitation of 4(5)-imidazole carboxylic acid imidazole is promoted by adding sodium nitrate solid 5, the addition of concentrated sulfuric acid and a sodium hydroxide solution for neutralizing concentrated sulfuric acid is reduced by adding a catalyst, reaction consumption is reduced, reaction efficiency is improved, reaction operation is simplified, and high industrial popularization value is achieved.

Description

Technical field: [0001] The invention relates to a synthesis method of 4(5)-hydroxymethylimidazole, which belongs to the field of chemical synthesis. Background technique: [0002] 4(5)-Hydroxymethylimidazole has a hydroxyl functional group, so it has both imidazole and alcohol properties, so it is widely used in chemical reactions, and 4(5)-Hydroxymethylimidazole has become an important chemical intermediate , The market application prospect is broad, and it is mainly used in the synthesis of important chemical products such as medicine, pesticide and resin. 4(5)-Hydroxymethylimidazole can synthesize farnesyltransferase inhibitors, which are widely used in medicine; indole and 4(5)-Hydroxymethylimidazole can synthesize conjugated compounds, which can effectively inhibit some The growth of drug-resistant genes in tumor cells, and the side effects are small, so it has a good application prospect in cancer treatment; it can be used to synthesize pesticides for resisting bacte...

Claims

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Application Information

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IPC IPC(8): C07D233/64
CPCC07D233/64
Inventor 胡海威丁靓闫永平郑辉严辉
Owner ITIC MEDCHEM CO LTD
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