Method for synthetizing fenflumizole

A technology of imidazole and difluorophenyl, which is applied in the field of organic chemical synthesis, can solve problems such as great danger, and achieve the effects of low cost, avoidance of use, and safe application

Inactive Publication Date: 2012-07-25
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This route requires the use of highly toxic KCN, which is more dangerous

Method used

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  • Method for synthetizing fenflumizole
  • Method for synthetizing fenflumizole
  • Method for synthetizing fenflumizole

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Step 1,1, the synthesis of 3-bis(4-methoxybenzene)-1,3 diketone

[0030]

[0031] Sodium hydride (60%, 4.0 g, 100 mmol) and dry tetrahydrofuran (50 mL) were added to a 250 mL one-necked flask. After stirring in ice bath for 20 min, methyl 4-methoxybenzoate (7.3 g, 44 mmol) was added, and then 4-methoxyacetophenone (6.0 g, 40 mmol) was added dropwise. After the dropwise addition was completed, the temperature was raised to 60° C. and stirred for 12 hours. After TLC (thin-layer chromatography) showed that the reaction was complete, water was added dropwise to the reaction system to quench the reaction, and dilute hydrochloric acid was added to adjust the pH to about 3, extracted three times with ethyl acetate, and dried over anhydrous sodium sulfate. The organic solvent was spin-off on a rotary evaporator, and the obtained crude product was recrystallized from a mixed solvent of petroleum ether and ethyl acetate to obtain 8.0 g of 1,3-bis(4-methoxybenzene)-1,3-dione a...

Embodiment 2

[0042] Step 1,1, the synthesis of 3-bis(4-methoxybenzene)-1,3 diketone

[0043] Sodium hydride (60%, 3.2g, 80mmol) and dry tetrahydrofuran (50mL) were added into a 250mL single-necked flask, and after stirring for 20min under ice bath, methyl 4-methoxybenzoate (3.3g, 20mmol) was added, and then Then 4-methoxyacetophenone (6.0 g, 40 mmol) was added dropwise. After the dropwise addition was completed, the temperature was raised to 60° C. and stirred for 12 hours. After TLC showed that the reaction was complete, water was added dropwise to the reaction system to quench the reaction, and the pH was adjusted to about 3 by adding dilute hydrochloric acid, extracted three times with ethyl acetate, and dried over anhydrous sodium sulfate. The organic solvent was spin-off on a rotary evaporator, and the obtained crude product was recrystallized from a mixed solvent of petroleum ether and ethyl acetate to obtain 3.9 g of 1,3-bis(4-methoxybenzene)-1,3-dione as a yellow solid. rate of 68...

Embodiment 3

[0049] Step 1,1, the synthesis of 3-bis(4-methoxybenzene)-1,3 diketone

[0050] Sodium hydride (60%, 6.4g, 160mmol) and dry tetrahydrofuran (50mL) were added into a 250mL single-necked flask, and after stirring for 20min under ice bath, methyl 4-methoxybenzoate (8.0g, 48mmol) was added, and then Then 4-methoxyacetophenone (6.0 g, 40 mmol) was added dropwise. After the dropwise addition was completed, the temperature was raised to 60° C. and stirred for 12 hours. After TLC showed that the reaction was complete, water was added dropwise to the reaction system to quench the reaction, and the pH was adjusted to about 3 by adding dilute hydrochloric acid, extracted three times with ethyl acetate, and dried over anhydrous sodium sulfate. The organic solvent was spin-off on a rotary evaporator, and the obtained crude product was recrystallized from a mixed solvent of petroleum ether and ethyl acetate to obtain 8.3 g of 1,3-bis(4-methoxybenzene)-1,3-dione as a yellow solid. rate of 7...

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Abstract

The invention discloses a method for synthetizing fenflumizole and belongs to the technical field of organic chemical synthesis. The method comprises the following steps: under the action of a catalyst, reacting methyl 4-methoxybenzoate with 4-methoxyacetophenone to generate 1,3-bis(4-metoxybenzene)-1,3 diketone; reacting with tert-butyl nitrite to generate 1,2-bis(4-metoxybenzene)-1,2 diketone; and reacting with 2,4-difluorine benzaldehyde to generate 2-(2,4-difluorophenyl)-4,5-bis(methoxyphenyl)-1H-imidazole. By the adoption of the method, 1,2-diketone is prepared from 1,3-diketone, so that the use of KCN (potassium cyanide) can be avoided.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing fenflumidazole Background technique [0002] Fenflumidazole, 2-(2,4-difluorophenyl)-4,5-bis(4-methoxyphenyl)-1H-imidazole, its structural formula is shown in formula (1), [0003] [0004] This compound is an important imidazole derivative with anti-inflammatory, analgesic and antipyretic effects (Pharmadynamics and toxicology of fenflumizote, a new non-steroidal anti-inflammatory imidazole derivative.Acta Pharmacol.Toxicol.53,288-296(1983)) . [0005] Compared with other NSAIDs, fenflumazole has better activity and lower side effects, especially gastrointestinal inflammation (Antithrombotic and Ulcerogenic Effects of Fenflumizole, a New Anti-Inflammatory Imidazole Derivative, in Rats, Japan. J. Pharmacol. 44, 93-96 (1987)). [0006] In addition, experiments and clinical studies have shown that fenflumizole also has antiplatelet ...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 梅光耀张玉红张勋斌谢永居黄乐浩
Owner ZHEJIANG UNIV
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