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Method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole

A technology of diphenylimidazole and triphenyloxazole, applied in the direction of organic chemistry, etc., to achieve the effects of simple operation, high practical value and short reaction time

Active Publication Date: 2015-04-22
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method of simultaneously generating imidazole and oxazole in the next step of diketone action has not been reported in the literature

Method used

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  • Method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole
  • Method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Synthesis reaction of 2-methyl-4,5-diphenylimidazole and 2,4,5-triphenyloxazole

[0021] Into a 50ml round-bottomed flask, 1mmol of benzophenone, 3mmol of butanedione, 10mmol of ammonium acetate and 15mL of absolute ethanol were added successively to the 50ml round-bottomed flask. After stirring, heat to 70~78℃ and keep the reaction solution until the end of the reaction. Reaction for 2h . After the reaction is completed, the reflux device is changed to a distillation device, the absolute ethanol is distilled off, and the residue is subjected to thin-layer chromatography, using a mixture of ethyl acetate and cyclohexane in a volume ratio of 1:4 as the eluent. 2-methyl-4,5-diphenylimidazole and 2,4,5-triphenyloxazole are obtained. The yield of 2-methyl-4,5-diphenylimidazole was 41%, and the yield of 2,4,5-triphenyloxazole was 44%.

[0022] The chemical reaction formula of the present invention is:

[0023]

Embodiment 2

[0024] Example 2 Product identification

[0025] Analyze and identify the products obtained from the above synthesis reaction by thin layer chromatography:

[0026] Analysis and identification of product one:

[0027] 1. Identification of physical and chemical properties:

[0028] White solid, mp: 113-115°C.

[0029] 2. 1 H NMR spectrum analysis:

[0030] 1 H NMR(600 MHz, CDCl 3 ) δ (ppm): 8.185 (s, 1H, ArH), 8.166 (s, 1H, ArH), 7.754 (s, 1H, ArH), 7.734 (s, 1H, ArH), 7.702 (s, 1H, ArH) , 7.681 (s, 1H, ArH), 7.488 (s, 1H, ArH), 7.482 (s, 2H, ArH), 7.353-7.421 (m, 6H, ArH).

[0031] 3. 13 C nuclear magnetic resonance spectrum analysis:

[0032] 13 C NMR (150 MHz, CDCl 3 ) δ (ppm): 160.124, 132.490, 130.367, 129.341, 129.039, 128.944, 128.752, 128.673, 128.608, 128.551, 128.234, 128.140, 127.313, 126.538, 126.465.

[0033] The above identification shows that the reaction product is 2,4,5-triphenyloxazole.

[0034] Analysis and identification of product two:

[0035] 1. Identification of phy...

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Abstract

The invention provides a new method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole in a reaction system at the same time. Benzil, butanedione and ammonium acetate with the molar ratio of 1:3:10 are added in absolute ethyl alcohol, after even stirring, the mixture is heated to 70-78 DEG C, the reaction solution is insulated till the reaction is finished, a reflux unit is changed into a distillation device, after solvent is steamed away, and the thin layer chromatography is carried out on residues to obtain 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole through separation. The method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole is easy to operate and has high practical value.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for simultaneously synthesizing 2-methyl-4,5-diphenylimidazole and 2,4,5-triphenyloxazole in a reaction system. Background technique [0002] Both imidazole and oxazole compounds are important organic compounds. As intermediates or final products, they are widely used in the fields of organic synthesis, drug synthesis, pesticides, papermaking and functional materials, especially in the production of fine chemicals. Occupies an extremely important position. For many years, the research on the synthetic methods of imidazole and oxazole compounds has been one of the hot topics in the field of organic chemistry. [0003] In the prior art, common methods for synthesizing imidazoles and oxazoles with substituents are all formed by ring closure of diketone and aldehyde under the action of amine (ammonium). The method of simultaneously generating imidazole and o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D263/32
CPCC07D233/58C07D263/32
Inventor 景崤壁陆海龙王磊谭晓东袁丹丹沈明
Owner YANGZHOU UNIV