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Synthesis method of suprofen drug intermediate 2-(p-fluorobenzoyl)thiophene

The technology of a fluorobenzoyl group and a synthesis method is applied in the field of synthesis of 2-thiophene, a drug intermediate of tibuprofen, and can solve the problems of reducing the sensitivity of pain receptors, so as to reduce the reaction temperature and reaction time, and improve the reaction yield. efficiency, reducing the effect of intermediate links

Inactive Publication Date: 2016-04-20
CHENGDU DONG DIAN AI ER TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The analgesic and anti-inflammatory mechanism of ibuprofen has not been fully elucidated. It may act on local inflammatory tissues by inhibiting the synthesis of prostaglandins or other transmitters. Due to the inhibition of leukocyte activity and release of lysosomal enzymes, local tissue Reduced pain impulses, decreased sensitivity of pain receptors

Method used

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  • Synthesis method of suprofen drug intermediate 2-(p-fluorobenzoyl)thiophene

Examples

Experimental program
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Effect test

example 1

[0011] In the reaction vessel equipped with stirrer, thermometer, and reflux condenser, add cuprous chloride 0.57mol, cyclohexane 350ml, control the stirring speed at 170rpm, drop by p-fluorobenzamide 0.58mol, thiophene 0.65mol, cyclohexane For a mixed solution of 230ml of hexane, the dropwise addition time is controlled at 2h, kept in a stirring state for 4h, and then refluxed for 4h. After most of the cyclohexane is evaporated, it is poured into a 35% sodium bromide solution with a mass fraction, and the temperature of the solution is kept at 2°C, the stirring speed was controlled at 230rpm, and after 30min, the nitromethane layer was extracted 5 times with a mass fraction of 65% nitromethane, and the nitromethane layer was successively extracted with a mass fraction of 7% sodium sulfite solution, a mass fraction of 17% sodium chloride solution, Phosphorus oxide was dehydrated, nitromethane was recovered, and recrystallized from toluene to obtain 102.75 g of light yellow crys...

example 2

[0013] In the reaction vessel equipped with stirrer, thermometer, and reflux condenser, add cuprous chloride 0.58mol, cyclohexane 380ml, control the stirring speed at 180rpm, drop by p-fluorobenzamide 0.58mol, thiophene 0.65mol, cyclohexane For a mixed solution of 230ml of hexane, the dropwise addition time is controlled at 2h, kept in a stirring state for 4h, and then refluxed for 4h. After most of the cyclohexane is evaporated, it is poured into a 38% sodium bromide solution with a mass fraction, and the temperature of the solution is kept at 3°C, the stirring speed was controlled at 250rpm, and after 35min, the nitromethane layer was extracted 6 times with a mass fraction of 67% nitromethane, and the nitromethane layer was successively oxidized with a mass fraction of 78% sodium sulfite solution, a mass fraction of 18% sodium chloride solution, and Calcium was dehydrated, nitromethane was recovered, and recrystallized with toluene to obtain 106.34 g of light yellow crystal 2...

example 3

[0015] In the reaction vessel equipped with stirrer, thermometer, and reflux condenser, add cuprous chloride 0.59mol, cyclohexane 400ml, control the stirring speed at 190rpm, drop by p-fluorobenzamide 0.58mol, thiophene 0.65mol, cyclohexane For a mixed solution of 230ml of hexane, the dropwise addition time is controlled at 3h, kept in a stirring state for 5h, and then refluxed for 4h. After most of the cyclohexane is evaporated, it is poured into a 40% sodium bromide solution with a mass fraction, and the temperature of the solution is kept at 5°C, the stirring speed was controlled at 260rpm, and after 40min, the nitromethane layer was extracted 7 times with a mass fraction of 70% nitromethane, and the nitromethane layer was successively extracted with a mass fraction of 80% sodium sulfite solution, a mass fraction of 20% sodium chloride solution, Phosphorus oxide was dehydrated, nitromethane was recovered, and recrystallized from toluene to obtain 109.92 g of light yellow cry...

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Abstract

A synthesis method of suprofen drug intermediate 2-(p-fluorobenzoyl)thiophene comprises steps as follows: 0.57-0.59 mol of cuprous chloride and 350-400 ml of cyclohexane are added to a reaction container provided with a stirrer, a thermometer and a reflux condenser, the stirring speed is controlled within 170-190 rpm, a mixed solution of 0.58 mol of p-fluorobenzamide, 0.65 mol of thiophene and 230 ml of cyclohexane is dropwise added, the addition time is controlled within 2-3 h, the stirring state is kept for 4-5 h, reflux is performed for 4 h, after most cyclohexane is evaporated out, a sodium bromide solution is poured into the container, the solution temperature is kept at 2-5 DEG C, the stirring speed is controlled within 230-260 rpm, after 30-40 min, extraction is performed with nitromethane for 5-7 times, a nitromethane layer is dehydrated with a sodiumsulfite solution, a sodium chloride solution and a dehydrating agent sequentially for recovery of nitromethane, recrystallization is performed with toluene, and light yellow 2-(p-fluorobenzoyl) thiophene crystals are obtained, wherein the mass fraction of the sodium bromide solution in the step is 35%-40%.

Description

technical field [0001] The invention relates to a method for synthesizing 2-(p-fluorobenzoyl)thiophene, a drug intermediate of thiabuprofen. Background technique [0002] Thiaprofen has anti-inflammatory, analgesic and antipyretic effects. It is slightly less effective than acetylsalicylic acid and phenylbutazone in the treatment of rheumatism and rheumatoid arthritis. It is suitable for the treatment of rheumatoid arthritis, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis and neuritis, etc. The analgesic and anti-inflammatory mechanism of ibuprofen has not been fully elucidated. It may act on local inflammatory tissues by inhibiting the synthesis of prostaglandins or other transmitters. Due to the inhibition of leukocyte activity and release of lysosomal enzymes, local tissue Reduced pain impulses and decreased sensitivity of pain receptors. The treatment of gout is through anti-inflammatory, analgesic, and hyperuricemia cannot be corrected. It can inhibit ...

Claims

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Application Information

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IPC IPC(8): C07D333/22
CPCC07D333/22C07B2200/13
Inventor 储冬红
Owner CHENGDU DONG DIAN AI ER TECH
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