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Method for preparing 2-phenylimidazole compounds

The technology of phenylimidazole and compound is applied in the field of compound preparation, can solve the problems of difficult pH value of reaction solution, severe reaction conditions, many by-products and the like, and achieves the effects of low production cost, simple operation and stable quality

Active Publication Date: 2012-07-25
浜田智子
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Problems solved by technology

[0003] The literature "Progress in the Synthesis of 2-Phenylimidazoles" ("Guangzhou Chemical Industry", Volume 37, Issue 3, 2009. Zhou Jialin, Fan Heping) reviewed various synthetic methods of 2-phenylimidazoles. Among these methods, the most The method of economic value is the synthetic method of the Debus method—the reaction of aldehydes and o-dicarbonyl compounds. Other methods or because of the severe reaction conditions, or because of the existence of side reactions, or because the yield is too low, are not economically suitable and only have Academic research value. However, there are not many literatures about the synthesis of 2-phenylimidazoles using this method
[0004] Patent Ger.offen2360175 (Frank Aton, Karn Helmut.Verfahren Zur Heratellung Von Imidazolen[P]) selects benzaldehyde, glyoxal to add ammonia water and pressurizes reaction in ethanol solvent to obtain 2-phenylimidazole. But this method needs to adjust three It is difficult to control the pH value of the reaction solution in operation. At the same time, according to practice, due to the high pH of the reaction solution, the 2-phenylimidazole produced by this method has a darker color and many by-products, so it is not easy to purify to obtain a suitable product. requested product.
[0005] In the patent US3715365 (Schuize.H.Imidazole synthesis [P].1973-02-06), glyoxal and the corresponding benzaldehyde are used in a strong acid ammonium salt solution to react under heating conditions to prepare 2-phenylimidazole. But , because the solubility of benzaldehyde in water is too low, this reaction is a two-phase reaction, the generated products are few, the yield is very low, and there are many by-products, which is not conducive to purification.
[0006] Patent JP6056961 (Nakayama Shigenobu; Noguchi Yoshiaki; Production of Imidazole[P].1985-04-02) uses ammonium carbonate instead of ammonia to inhibit the synthesis of by-products under high concentration conditions. Although it has been improved, there are still produced products Very little, the yield is very low, and there are many by-products, which is not conducive to the problem of purification

Method used

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  • Method for preparing 2-phenylimidazole compounds
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Examples

Experimental program
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Effect test

Embodiment 1

[0036] In a 1000mL four-necked bottle, equipped with a thermometer, an electric stirrer, and a reflux condenser, add 200g of water, 63g of ammonium carbonate, 200g of methanol, and 46.4g of benzaldehyde, stir, heat up in a water bath, and keep the internal temperature at 35-40°C .Mix 112.5g of 28% methylglyoxal and 112g of methanol evenly, place it in a 200mL constant-pressure dropping funnel, add it dropwise to the reaction solution within 4.5 hours, and then keep the internal temperature at 35-40°C for 1 hour. Sampling for HPLC analysis It shows that the product content is 92.4184% (Area%).

[0037] After the reaction was finished, the reaction solution was concentrated to dryness under reduced pressure and methanol was recovered. 150 g of water was added to the residue, stirred evenly and cooled to crystallize, filtered, and the solid was washed twice with 25 g × 2 water, and dried to obtain 57.4 g of a yellow crude product. The yield of the crude product based on benzaldeh...

Embodiment 2

[0039] In a 500mL four-necked bottle, equipped with a thermometer, an electric stirrer, and a reflux condenser, add 30g of water, 42g of ammonium carbonate, 100g of methanol, and 46.4g of benzaldehyde, stir, heat up in a water bath, and keep the internal temperature at 35-40°C . Mix 112.5 g of 28% methylglyoxal and 60 g of methanol evenly, place it in a 200 mL constant pressure dropping funnel, and drop it into the reaction solution within 4.5 hours. When the remaining 10% of the dropwise mixed liquid was added, 8.4 g of ammonium carbonate was added. Then keep the internal temperature at 35-40° C. for 1 hour. Sample HPLC analysis showed that the product content was 94.5558% (Area%).

[0040]After the reaction, the reaction solution was concentrated to dryness under reduced pressure and methanol was recovered. Add 150g of water to the residue, stir evenly and cool down to crystallize, filter, wash the solid twice with 25g×2 water, and dry to obtain 63.4g of a yellow crude pr...

Embodiment 3

[0042] In a 1000mL four-necked bottle, equipped with a thermometer, an electric stirrer, and a reflux condenser, add 120g of water, 63g of ammonium carbonate, 100g of methanol, and 46.4g of benzaldehyde, stir, heat up in a water bath, and keep the inner temperature at 35-40°C .Mix 112.5g of 28% methylglyoxal and 112g of methanol evenly, place in a 200mL constant pressure dropping funnel, add dropwise to the reaction solution within 4.5 hours, and then keep the internal temperature at 35-40°C for 8 hours.

[0043] After the reaction was finished, the reaction solution was concentrated to dryness under reduced pressure and methanol was recovered. Add 150 g of water to the residue, stir evenly and cool down to crystallize, filter, wash the solid twice with 25 g×2 water, and obtain 60.4 g of a yellow crude product after drying. The yield of the crude product based on benzaldehyde was 87.32%. The analysis result of the crude product was 96.8605% (Area%).

[0044] Using self-made wh...

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Abstract

The invention discloses a method for preparing 2-phenylimidazole compounds. The method comprises the following steps: preparing ortho-dicarbonyl compounds or a mixture of the ortho-dicarbonyl compounds and an organic solvent; preparing benzaldehyde or a mixture of substituted benzaldehyde, ammonia or ammonium salt; dropwise adding the ortho-dicarbonyl compounds or the mixture of the ortho-dicarbonyl compounds and the organic solvent into the benzaldehyde or the mixture of the substituted benzaldehyde, the ammonia or the ammonium salt, wherein the reaction temperature is between 0 and 100 DEG C, and the reaction pressure is between 0.1 and 2MPa; obtaining a crude product of the 2-phenylimidazole compounds after reaction; and purifying the crude product of the 2-phenylimidazole compounds byadopting halohydrocarbon or alkenyl halides so as to prepare high purity 2-phenylimidazole compounds. The preparation method has simple operation and low cost, and the produced 2-phenylimidazole compounds have high purity.

Description

technical field [0001] The invention relates to a preparation method of compounds, in particular to a preparation method of 2-phenylimidazole compounds. Background technique [0002] Due to the widespread use and economic importance of 2-phenylimidazoles, various methods for the synthesis of 2-phenylimidazoles have been developed. [0003] The literature "Progress in the Synthesis of 2-Phenylimidazoles" ("Guangzhou Chemical Industry", Volume 37, Issue 3, 2009. Zhou Jialin, Fan Heping) reviewed various synthetic methods of 2-phenylimidazoles. Among these methods, the most The method of economic value is the synthetic method of the Debus method—the reaction of aldehydes and o-dicarbonyl compounds. Other methods or because of the severe reaction conditions, or because of the existence of side reactions, or because the yield is too low, are not economically suitable and only have Academic research value. However, there are not many literatures about the synthesis of 2-phenylimi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/58C07D233/64
Inventor 浜田申一浜田智子唐成见
Owner 浜田智子
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