Method for synthesizing 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole

A synthesis method and a diphenyl technology, which are applied in the field of synthesis of 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole, can solve problems such as lack, and achieve Moderate polarity, high purity, good effect of separating and purifying products

Inactive Publication Date: 2015-04-29
YANGZHOU UNIV
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Problems solved by technology

[0003] At present, there is a lack of a synthetic method for 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole with simple process and high product purity

Method used

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  • Method for synthesizing 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole

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Embodiment 1

[0014] General reaction formula of the present invention is:

[0015]

[0016] The present invention provides a synthesis method of 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole, adding 1mmol 1,2-diazole to a 50ml round bottom flask successively Phenylacrylonitrile, 2mmol potassium carbonate, 2mmol sodium azide, 0.2mmol cuprous iodide and 10ml DMSO, heated to 100°C for reaction, after 3h the reaction was completed, cooled, the system was poured into 100ml water, the mixture was washed with ethyl acetate The ester was extracted 2-3 times, and the solvent was evaporated after merging the organic layers, and the residue was subjected to thin chromatography, and the column chromatography adopted a silica gel stationary phase, and the eluent was a mixture of ethyl acetate and cyclohexane, and the ethyl acetate and The mixing volume ratio of cyclohexane is 1:4. 4,5-Diphenyl-1,4,5-trihydro-1,2,3-triazole was isolated.

[0017] The molar ratio of the 1,2-diphenylacrylonitrile, potas...

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Abstract

The invention discloses a method for synthesizing 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole. The method comprises the following steps of firstly mixing 1,2-diphenyl-acrylonitrile, potassium carbonate, sodium azide, cuprous iodide and dimethyl sulfoxide DMSO, stirring and heating to 95-105 DEG C, reacting for 3-3.5 hours, after the reaction is completed, adding water to obtain a mixture, extracting the mixture, distilling to remove the solvent, purifying the residue by column chromatography to obtain 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole, wherein the feeding molar ratio of 1,2-diphenyl-acrylonitrile, potassium carbonate, sodium azide and cuprous iodide is 1:2:2:0.2. The reaction time and the reaction temperature adopted in the invention are more suitable reaction time and temperature, too high temperature, the ratio of reaction byproducts too high, if the temperature is too low, the reaction cannot be carried out; if the reaction time is shortened, the incomplete reaction can be caused and the reaction time is prolonged, the yield of the byproducts is high.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a synthesis method of 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole. Background technique [0002] 1,2,3-Triazole ring is a very important five-membered heterocyclic compound, which has attracted much attention because of its good pharmacological activity. It has been reported in the literature that there are many synthetic methods, such as NH-1,2,3-triazole synthesized by cycloaddition of tri-n-butyltin azide and monosubstituted or disubstituted alkynes under appropriate pressure and heating conditions. The yield was only (30-67%). Furthermore, tri-n-butyltin azide is relatively expensive. We used relatively safe sodium azide to react with 1,2-diphenylacrylonitrile to generate 4,5-diphenyl-1,4,5-trihydro-1,2,3-triazole, and Compared with other methods, our method has the characteristics of mild reaction, simple reaction conditions, and cheap raw materials. In the prior art, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06
CPCC07D249/06
Inventor 景崤壁陆海龙王磊谭晓东袁丹丹沈明
Owner YANGZHOU UNIV
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