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Synthesis method of 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole

A trifluoromethyl and methanesulfonyl technology, applied in the field of organic chemical synthesis, can solve the problems of poor reaction repeatability, carbon-carbon double bond breakage, difficulty in amplification, etc., and achieve the effects of less by-products, low cost, and avoiding damage

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

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Problems solved by technology

The former method has poor reaction repeatability in the benzoin condensation step, and it is difficult to scale up, and highly toxic HCN is produced during the hydrolysis process, which limits the application of this method; the latter two methods use KMnO 4 When oxidized, it may cause the breakage of the carbon-carbon double bond

Method used

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  • Synthesis method of 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole
  • Synthesis method of 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole
  • Synthesis method of 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Synthesis of step 1 4-methylthioacetophenone

[0040]

[0041] Add sulfide anisole (25g, 200mmol) and dichloromethane (150mL) in 250mL round-bottomed flask; Add aluminum trichloride (40g, 300mmol) thereinto under stirring condition at 0 ℃, then slowly dropwise add acetyl chloride ( 16g, 15mL, 200mmol); after the dropwise addition was completed, it was naturally raised to room temperature and stirred for 12 hours. TLC (thin layer chromatography) showed that after the reaction was completed, the reaction solution was poured into crushed ice, and concentrated hydrochloric acid was added to adjust the pH to about 2. Stir at room temperature for 15 min, extract three times with dichloromethane, and combine the organic phases. The organic phase was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was spun off on a rotary evaporator, and the obtained crude product was recrystallized with a mixed solvent of pe...

Embodiment 2

[0060] Synthesis of step 1 4-methylthioacetophenone

[0061] Add sulfide anisole (25g, 200mmol) and dichloromethane (150mL) in 250mL round-bottomed flask; Add iron trichloride (80g, 500mmol) therein under stirring condition at 0 ℃, then slowly add acetyl chloride ( 32g, 30mL, 400mmol); after the dropwise addition was completed, it was naturally raised to room temperature and stirred for 12 hours. TLC showed that after the reaction was completed, the reaction solution was poured into crushed ice, and concentrated hydrochloric acid was added to adjust the pH to about 2. Stir at room temperature for 15 min, extract three times with dichloromethane, and combine the organic phases. The organic phase was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was spun off on a rotary evaporator, and the obtained crude product was recrystallized from a mixed solvent of petroleum ether and ethyl acetate to obtain 14 g of white...

Embodiment 3

[0071] Synthesis of step 1 4-methylthioacetophenone

[0072] Add sulfide anisole (25g, 200mmol) and chloroform (150mL) in 250mL round-bottomed flask; Add aluminum trichloride (32g, 240mmol) therein under stirring condition at 0 ℃, then slowly add acetyl chloride ( 8g, 7.5mL, 100mmol); after the dropwise addition, it was naturally raised to room temperature and stirred for 12 hours. TLC showed that after the reaction was completed, the reaction solution was poured into crushed ice, and concentrated hydrochloric acid was added to adjust the pH to about 2. Stir at room temperature for 15 min, extract three times with dichloromethane, and combine the organic phases. The organic phase was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The organic solvent was spun off on a rotary evaporator, and the obtained crude product was recrystallized with a mixed solvent of petroleum ether and ethyl acetate to obtain 17 g of white solid 4-methyl...

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Abstract

The invention discloses a novel synthesis method of 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole and belongs to the technical field of organic chemical synthesis. The method comprises the following steps: carrying out reaction on thioanisole and acetyl chloride to generate 4-methylthioacetophenone, carrying out reaction on 4-methylthioacetophenone and methyl benzoate to generate 1-(4-methylthiophenyl)-3-phenyl-1,3-dione, carrying out reaction on 1-(4-methylthiophenyl)-3-phenyl-1,3-dione and tert-butyl nitrite to generate 1-(4-methylthiophenyl)-2-phenyl-1,2-dione, carrying out reaction on 1-(4-methylthiophenyl)-2-phenyl-1,2-dione and trifluoroacetaldehyde methyl hemiacetal to generate 4-[4-(methylthio)phenyl]-5-phenyl-2-(thrifluoromethyl)-1H-imidazole, and finally oxidizing to generate 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole. According to the invention, the synthesis method is adopted, the utilization of cyanide and the damage of KMnO4 to carbon-carbon double bond are avoided, so that the method has industrial application values.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing 4-[4-(methylsulfonyl)phenyl]-5-phenyl-2-(trifluoromethyl)-1H-imidazole. Background technique [0002] Prostaglandins play an important role in the production of inflammation, and inhibiting the production of prostaglandins is a basic way of anti-inflammatory drugs. But while common NSAIDs block inflammation by inhibiting prostaglandins, they also inhibit the normal physiological regulation of prostaglandins. Therefore, the use of high doses of anti-inflammatory drugs can lead to side effects, especially severe ulcers. Traditional NSAIDs work by blocking inflammation by inhibiting cyclooxygenase (COX), an enzyme involved in the production of prostaglandins. [0003] Studies have shown that replacing COX by inhibiting another enzyme cyclooxygenase II (COX II) can achieve the purpose of preventing inflammation more efficiently and have ...

Claims

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Application Information

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