CN101768092A - Preparation method of intermediate of non-steroidal anti-inflammatory drug - Google Patents
Preparation method of intermediate of non-steroidal anti-inflammatory drug Download PDFInfo
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- CN101768092A CN101768092A CN200910067622A CN200910067622A CN101768092A CN 101768092 A CN101768092 A CN 101768092A CN 200910067622 A CN200910067622 A CN 200910067622A CN 200910067622 A CN200910067622 A CN 200910067622A CN 101768092 A CN101768092 A CN 101768092A
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- preparation
- methane
- phenoxy group
- nimesulide
- inflammatory drug
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of an intermediate of a non-steroidal anti-inflammatory drug, in particular to the preparation method of a nimesulide intermediate of 2-phenoxy-methane-sulfonyl aniline. The preparation method of the nimesulide intermediate of the 2-phenoxy-methane-sulfonyl aniline comprises the following steps: adding o-amino diphenyl ether (I) into a reactor which is provided with a drying and condensing device, adding an organic solvent, continuously adding methanesulfonyl chloride within one hour of heating, filtering and drying mixture, and obtaining 2-phenoxy methanesulfonyl chloride (II).
Description
Technical field
The present invention relates to the preparation method of nonsteroidal anti-inflammatory drug nimesulide, the preparation method of the nimesulide intermediate 2-phenoxy group sulfonyl methane aniline of more specifically saying so.
Background technology
Nimesulide is a kind of novel NSAID (non-steroidal anti-inflammatory drug), has analgesic and analgesic activities.The preparation method of disclosed compound (II) joined methane sulfonyl chloride in the pyridine solution of adjacent amino-diphenylethers in three hours, be poured into then in 5L ice and the 2L concentrated hydrochloric acid mixed solution, filter, with the crude product 2-phenoxy group sulfonyl methane aniline of 100% salt acid elution, use the mixture recrystallization of ethanol and water again.This method preparation time is long, reactions steps is many, and cost is higher, and pyridine foul smelling flavor, and polluted air can't satisfy the large-scale industrialization production requirement, therefore is necessary this method is improved.
Summary of the invention
The present invention is intended to overcome deficiency of the prior art, and a kind of simple and convenient process for preparing that is suitable for suitability for industrialized production body 2-phenoxy group sulfonyl methane aniline is provided.
Preparation scheme of the present invention is as follows:
The preparation method of nimesulide intermediate 2-phenoxy group sulfonyl methane aniline, adjacent amino-diphenylethers (I) is joined in the reactor that drying, condensing works are housed, add organic solvent, heating, continuing to add methane sulfonyl chloride in one hour reacts, mixture is filtered, dries, obtain 2-phenoxy group methane sulfonyl chloride (II).
Molten or triethylamine liquid is stirred and heated to 80 ℃ with adjacent amino-diphenylethers (I) ethyl acetate; The mass percent of ethyl acetate or triethylamine and adjacent amino-diphenylethers (I) mixture is 80% (W/W), preferably maintain the temperature at 87 ℃, continue to add methane sulfonyl chloride in one hour and react, mixture is filtered, dries, obtain 2-phenoxy group methane sulfonyl chloride (II).
The invention has the advantages that and do not use pyridine, avoided the recrystallization of the mixture of concentrated hydrochloric acid washing and ethanol and water like this as solvent.Shorten reactions steps, saved the reaction times, the 2-phenoxy group methane sulfonyl chloride yield height that present method obtains, and cost is lower, is fit to large-scale industrialization production.
Embodiment
The invention will be further described below in conjunction with embodiment, but do not limit the present invention.
Embodiment 1. adds the 10L ethyl acetate solution that contains adjacent amino-diphenylethers 1300 grams and restrains in 80 ℃ of dropping methane sulfonyl chlorides 831 in the there-necked flask that mechanical stirring and drying tube 3L are housed, and reacts 2 hours.Cooling, stirring are filtered, and oven dry gets 2-phenoxy group sulfonyl methane aniline.Yield is 85%.
Claims (3)
1. the preparation method of nimesulide intermediate 2-phenoxy group sulfonyl methane aniline, it is characterized in that: adjacent amino-diphenylethers (I) organic solution solution joins in the reactor that drying, condensing works are housed, heat in one hour and to continue to add methane sulfonyl chloride and react, with in the mixture impouring frozen water, filter, oven dry, obtain 2-phenoxy group methane sulfonyl chloride (II).
2. the preparation method of nimesulide intermediate 2-phenoxy group sulfonyl methane aniline according to claim 1 is characterized in that described Heating temperature is 87 ℃.
3. the solution of compound according to claim 1 (I), the mass percent that it is characterized in that described ethyl acetate or triethylamine and compound (I) are 80% (W/W).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910067622A CN101768092A (en) | 2009-01-06 | 2009-01-06 | Preparation method of intermediate of non-steroidal anti-inflammatory drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910067622A CN101768092A (en) | 2009-01-06 | 2009-01-06 | Preparation method of intermediate of non-steroidal anti-inflammatory drug |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101768092A true CN101768092A (en) | 2010-07-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200910067622A Pending CN101768092A (en) | 2009-01-06 | 2009-01-06 | Preparation method of intermediate of non-steroidal anti-inflammatory drug |
Country Status (1)
| Country | Link |
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| CN (1) | CN101768092A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070471A (en) * | 2011-01-14 | 2011-05-25 | 荆州市丽之源化工科技有限公司 | Medicine intermediate 2-phenoxy aniline and preparation method thereof |
-
2009
- 2009-01-06 CN CN200910067622A patent/CN101768092A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070471A (en) * | 2011-01-14 | 2011-05-25 | 荆州市丽之源化工科技有限公司 | Medicine intermediate 2-phenoxy aniline and preparation method thereof |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20100707 |