Preparing process of 5-propionyl-2-thiophenyl phenylacetate

A technology of phenylthiophenylacetate and phenylacetate, which is applied in the field of preparation of 5-propionyl-2-phenylthiophenylacetate and can solve the problem of troublesome solid separation, incomplete reaction and low yield And other issues

Inactive Publication Date: 2008-09-03
常州市康瑞化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above two patent documents, since no solvent is used in the acylation reaction process, the mixing effect between the reactants is poor, which brings the disadvantages of incomplete reaction and low yield, and the separation of products is difficult, the post-treatment is complicated, and ice decomposition is required. After cooling, crystallization, suction filtration, water washing, recrystallization and other procedures, solid separation is very troublesome
In addition, in the reaction of preparing (13) from (11), the reaction conditions of water system and high temperature and high pressure are used, which is not suitable for industrial production; according to the preparation method provided by this patent document, many experiments are carried out, and the yield is very low

Method used

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  • Preparing process of 5-propionyl-2-thiophenyl phenylacetate
  • Preparing process of 5-propionyl-2-thiophenyl phenylacetate
  • Preparing process of 5-propionyl-2-thiophenyl phenylacetate

Examples

Experimental program
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Effect test

Embodiment 1

[0091] 1, the preparation of methyl o-chlorophenylacetate (15)

[0092] Raw material specification and feeding amount

[0093] Raw material (molecular weight)

Specification

Feeding amount

o-Chlorophenylacetic acid (170.5)

Industrial first-class product, white with acetic acid smell

Color powder.MP95~97℃

10Kg

Methanol(32)

Colorless, transparent, flammable and volatile polar liquid

Body ≥ 99%

19Kg

Concentrated sulfuric acid (98)

Colorless transparent oily liquid, strong corrosion,

Content≥98%

1.14Kg

[0094] Feeding ratio (molar ratio):

[0095] O-chlorophenylacetic acid: methanol: concentrated sulfuric acid = 1: 10.12: 0.20

[0096] Add o-chlorophenylacetic acid and methanol to the reaction kettle respectively, stir, add concentrated sulfuric acid dropwise under cooling, heat up and reflux for 10 hours, and remove the solvent. Add water, separate layers, neutralize the or...

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Abstract

The process of preparing 5-propionyl-2-thiophenyl phenylacetate as the medicine intermediate oof zaltoprofen includes the following steps: Friedel-Crafts reaction of o-chloro phenylacetate and propionyl chloride in solvent to obtain 5-propionyl-2-chloro phenylacetic ester, hydrolysis of 5-propionyl-2-chloro phenylacetic ester in water solution of alkali metal hydroxide to produce 5-propionyl-2-chloro phenylacetate, the Ullmann condensation with thiophenol under the action of dehydrant and catalyst to obtain 5-propionyl-2-thiophenyl phenylacetic acid, and final esterification with alcohol to obtain 5-propionyl-2-thiophenyl phenylacetate. The present invention has the advantages of high yield, low cost, simple post-treatment and no environmental pollution, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to the preparation method of 5-propionyl-2-phenylthiophenylacetate, and 5-propionyl-2-phenylthiophenylacetate is used for preparing "Zaltoprofen (Zaltoprofen"), namely A very important intermediate of 2-(10-oxo-10,11 dihydrodibenzo[b,f]thiazin-2-yl)propionic acid. Background technique [0002] Zaltoprofen is a potent non-steroidal anti-inflammatory, analgesic, and antipyretic drug. It acts selectively on the site of inflammation and has no effect on other organs such as stomach and kidney. Compared with similar drugs such as naproxen and ibuprofen, it has the characteristics of high efficiency and less gastric side effects. Its structural formula is as follows: [0003] [0004] 5-propionyl-2-phenylthiophenylacetate is a kind of very important pharmaceutical intermediate for preparing zaltoprofen at present, Japanese Patent Application No. 61-50961 and Patent Application Publication No. 6-228085. Methyl chlorophenyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C321/30C07D337/14
Inventor 陈文华袁根林
Owner 常州市康瑞化工有限公司
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