Method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole

A synthetic method, methylsulfonyl technology, applied in the field of organic chemical synthesis, can solve the problems of limited industrial application, explosion hazard, etc., and achieve low cost, high yield, and environmental friendliness

Inactive Publication Date: 2014-07-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This synthesis method requires the use of azide reagents, which has the risk of explosion and limits the industrial application

Method used

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  • Method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole
  • Method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole
  • Method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of step 1,4-methylthioacetophenone

[0036]

[0037] Add sulfide anisole (25g, 200mmol) and dichloromethane (150mL) in 250mL round-bottomed flask, add aluminum trichloride (40g, 300mmol) therein under stirring condition at 0 ℃, then slowly 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 then concentrated hydrochloric acid was added to reach a pH of 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 petrole...

Embodiment 2

[0056] The synthesis of step 1,4-methylthioacetophenone

[0057] 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. After TLC showed that the reaction was over, the reaction solution was poured into crushed ice, and then concentrated hydrochloric acid was added. 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 solid 4-methylthioaceto...

Embodiment 3

[0067] The synthesis of step 1,4-methylthioacetophenone

[0068] 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 was completed, it was naturally raised to room temperature and stirred for 12 hours. After TLC showed that the reaction was over, the reaction solution was poured into crushed ice, and then concentrated hydrochloric acid was added. 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 17 g of white solid 4-methylthioacetop...

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Abstract

The invention discloses a method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole. The method includes: thioanisole is reacted with acetyl chloride to generate 4-methylthio acetophenone which is reacted with 4-methyl fluorobenzoate to generate 1-(4-fluorophenyl)-3-(4-methylthio benzene)-1,3 diketone which is reacted with tert-butyl nitrite to generate 1-(4-fluorophenyl)-2-(4-methylthio benzene)-1,2 diketone which is reacted with 2-chlorobenzaldehyde to generate 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(methylthio) phenyl]thiazole which is oxidized to generate 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(mesyl) phenyl] thiazole. The method avoids usage of nitrine reagent and has important application value.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing 2-(2-chlorophenyl)-4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]thiazole . 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. Studies have shown that replacing COX by inhibiting another enzyme cyclooxygenase II (COX II) can achieve the purpose of preventing inflammation more efficiently and with few...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/26
Inventor 张玉红张勋斌谢永居黄乐浩
Owner ZHEJIANG UNIV
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