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Preparation method of 4-phenylimidazole

A technology of phenylimidazole and preparation steps, which is applied in the field of preparation of 4-phenylimidazole, can solve the problems of high price, low yield, few and the like, and achieves the effects of improving yield, high yield and easy control

Active Publication Date: 2021-01-22
SUZHOU YACOO SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

4-Phenylimidazole, as the basic raw material of central nervous system and metabolic disorder drugs, is widely used in the medical industry, but the price is relatively expensive, and there are few literature reports on the synthesis of 4-phenylimidazole
[0003] In the patent CN103450089B, α-bromoacetophenone and formamidine acetate are used to carry out substitution reaction in ethylene glycol, and then carry out cyclization reaction with acid-binding agent potassium carbonate, and then undergo post-treatment to obtain 4-phenylimidazole, but its low yield

Method used

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  • Preparation method of 4-phenylimidazole
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  • Preparation method of 4-phenylimidazole

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Experimental program
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Effect test

Embodiment 1

[0045] A kind of preparation method of 4-phenylimidazole comprises following preparation steps:

[0046] In a stainless steel reaction kettle, add 106g compound 1A benzaldehyde, compound 1B (NH 4 ) 2 CO 3 , nitrogen-containing compound sodium cyanide, the molar ratio of the above compound 1A, compound 1B, and nitrogen-containing compound is 1:1.1:1.1, stir evenly, and react for 24 hours at a temperature of 100°C and a pressure of 0.5MPa to obtain intermediate body;

[0047] The reducing agent sodium borohydride is passed into the intermediate body, the molar ratio of the above-mentioned intermediate and reducing agent is 1:3, under the condition that the temperature is 60° C. and the pressure is 0 MPa, react for 48 hours to obtain the crude 4-phenylimidazole, The total yield is about 78.6%;

[0048] Under dry conditions, dissolve 100g of crude 4-phenylimidazole in 400ml of ethanol, carry out low-temperature recrystallization, and then filter to remove insoluble matter, the...

Embodiment 2

[0050] A kind of preparation method of 4-phenylimidazole comprises following preparation steps:

[0051] In the stainless steel reactor, add the mixture of 122g compound 1A benzoic acid, compound 1B triphosgene, nitrogenous compound hydrocyanic acid and ammoniacal liquor successively, the mol ratio of above-mentioned compound 1A, compound 1B, nitrogenous compound is 1:1.3:1.3, Stir evenly, and react for 24 hours at a temperature of 80°C and a pressure of 0.3 MPa to obtain an intermediate;

[0052] The reducing reagent hydrogen is passed into the intermediate body, the molar ratio of the above-mentioned intermediate and the reducing reagent is 1:8, under the condition that the temperature is 60° C. and the pressure is 0.6 MPa, the reaction is carried out for 48 hours to obtain the crude 4-phenylimidazole. The yield is about 80.5%;

[0053] Under dry conditions, dissolve 100g of crude 4-phenylimidazole in 400ml of ethanol, carry out low-temperature recrystallization, and then fil...

Embodiment 3

[0055] A kind of preparation method of 4-phenylimidazole comprises following preparation steps:

[0056] In a stainless steel reaction kettle, add 138g compound 1A benzaldehyde, compound 1B NH 4 HCO 3 , nitrogen-containing compound sodium cyanide, the molar ratio of the above compound 1A, compound 1B, and nitrogen-containing compound is 1:1.1:1.1, stir evenly, and react for 24 hours at a temperature of 120°C and a pressure of 0.3MPa to obtain intermediate body;

[0057] The reducing agent potassium borohydride is introduced into the intermediate body, the molar ratio of the above-mentioned intermediate and reducing agent is 1:3, and the reaction is carried out for 48 hours at a temperature of 50°C and a pressure of 0.1MPa to obtain the crude 4-phenylimidazole , the total yield is about 76.3%;

[0058] Under dry conditions, dissolve 100g of crude 4-phenylimidazole in 400ml of ethanol, carry out low-temperature recrystallization, and then filter to remove insoluble matter, th...

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Abstract

The invention discloses a preparation method of 4-phenylimidazole, which comprises the following steps: reacting a compound 1A, a compound 1B and a nitrogen-containing compound to obtain an intermediate; and reacting the intermediate with a reducing agent to obtain a crude product of 4-phenylimidazole, and performing purifying to obtain a refined product of 4-phenylimidazole. According to the preparation method, a reagent with relatively low price is used as a starting raw material, a final product is obtained through two-step reaction, the reaction condition of each step is mild, the yield ofthe obtained 4-phenyl imidazole is high, and the cost can be greatly reduced.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-phenylimidazole. Background technique [0002] 4-phenylimidazole, CAS No. 670-95-1, its molecular structure is It is an epoxy curing imidazole accelerator and an intermediate in organic synthesis. 4-Phenylimidazole, as the basic raw material of drugs for central nervous system and metabolic disorders, is widely used in the medical industry, but the price is relatively expensive. Currently, there are few literature reports on the synthesis of 4-phenylimidazole. [0003] In the patent CN103450089B, α-bromoacetophenone and formamidine acetate are used to carry out substitution reaction in ethylene glycol, and then carry out cyclization reaction with acid-binding agent potassium carbonate, and then undergo post-treatment to obtain 4-phenylimidazole, but its The yield is lower. [0004] Therefore, it is of great significance to seek a new prepar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58
CPCC07D233/58Y02P20/584
Inventor 袁永坤蒋玉贵
Owner SUZHOU YACOO SCI CO LTD