CN1434031A - 2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof - Google Patents
2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof Download PDFInfo
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- CN1434031A CN1434031A CN 03118594 CN03118594A CN1434031A CN 1434031 A CN1434031 A CN 1434031A CN 03118594 CN03118594 CN 03118594 CN 03118594 A CN03118594 A CN 03118594A CN 1434031 A CN1434031 A CN 1434031A
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Abstract
The present invention relates to 2,5-dimethoxy-4-ethylthio-beta-nito-styrene and its method for preparing the above-mentioned compound. Said invention provides its structure formula and uses 2.5-dimethoxybenzenesulfonyl chloride as raw material, and adopts the following steps: using zinc powder to make reductino under the acidic condition at 70-80 deg.C, reduced pressure distilling to obtain 2,5-dimethoxythiophenol, making it and bromoethane undergo the process of condensation reaction under the alkaline condition at 70-80 deg.C, reduced pressure distilling to obtain 2.5-dimethoxyethyl phenyl sulfide, making it and phosphorus oxychloride and dimethyl formamide produce reaction at 70-80 deg.C to obtain 2,5-dimethoxy-4-ethylthiobenzaldehyde.
Description
Technical field
The present invention relates to 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene and method for making thereof and purposes.
Background technology
As a kind of new compound, 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene and synthetic method thereof are not seen bibliographical information as yet.
Summary of the invention
Task of the present invention provides a kind of new compound 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene and method for making thereof and purposes.
Technical scheme provided by the invention is: 2, and 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene, its structural formula is
The present invention also provides the method for making of above-claimed cpd, and with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions (pH＜1), uses zinc powder reduction, and underpressure distillation then obtains 2,5-dimethoxy thiophenol; Gained 2,5-dimethoxy thiophenol are at 70～80 ℃, alkaline condition (pH＞10) down and the monobromethane condensation, get 2 through underpressure distillation, 5-dimethoxy ethyl phenyl sulfide; 2,5-dimethoxy ethyl phenyl sulfide and phosphorus oxychloride and dimethyl formamide react under 70～80 ℃ of conditions and obtain 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde, products therefrom obtains 2 with the Nitromethane 99Min. condensation again, 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene.
2,5-dimethoxy benzene sulfonyl chloride can make by following method, and ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill yellow solid 2,5-dimethoxy benzene sulfonyl chloride.
The reaction equation of said process is as follows:
2 of the present invention's preparation, 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene is used to prepare 2,5-dimethoxy-4 '-ethyl phenyl sulfide ethamine.
Embodiment
In the 250ml there-necked flask, add 105ml ethylene dichloride, 13.5g terephthaldehyde ether, stirring and dissolving, ice bath cooling (0～10 ℃), stir and drip 26.5ml chlorsulfonic acid and 10ml sulfur oxychloride down, reacted 2 hours, and with in its impouring 280ml frozen water, told lower floor's oil reservoir under stirring, steam and remove methylene dichloride (recovery), get yellow solid 2,5-dimethoxy benzene sulfonyl chloride, oven-dried weight 19.8g, productive rate 85%, fusing point 115-117 ℃.
In the 500ml there-necked flask, add the 68ml water and the 23ml vitriol oil, when treating that temperature drops to about 70 ℃, adding 12g 2,5-dimethoxy benzene sulfonyl chloride and 18g zinc powder reacted 1 hour down at 80 ℃, and filtration, decompression, steaming are slipped and are obtained 8.2g 2,5-dimethoxy thiophenol.
In the 250ml there-necked flask, add 3g potassium hydroxide and 50ml dehydrated alcohol, stirring and dissolving adds 8g 2, and 5-dimethoxy thiophenol is dissolved in the solution of 20ml dehydrated alcohol, drip the 9g monobromethane again, reflux 1.5h boils off ethanol, uses twice of 40ml dichloromethane extraction, steam except that behind the methylene dichloride, underpressure distillation gets light yellow oily liquid 2,5-dimethoxy ethyl phenyl sulfide 8.2g, productive rate 80%.
Under the ice bath cooling, the 9.7ml phosphorus oxychloride is joined in the 100ml there-necked flask, drip the 11.5ml dimethyl formamide, drip 8g 2 again, 5-dimethoxy ethyl phenyl sulfide, 75 ℃ of stirring reactions 1 hour, placement is spent the night, suction filtration gets light yellow solid (is white solid through the Virahol recrystallization) 8.8g, and this compound is 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde.
Add 8g 2 in the 100ml there-necked flask, 5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde, 20ml Nitromethane 99Min. add 0.5g anhydrous acetic acid ammonium after the heating for dissolving, backflow 1.5h, separate out red solid 2 after the cooling, 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene 8.5g, productive rate 78.2%.
Under the ice bath cooling, in the 500ml there-necked flask, add 210ml anhydrous tetrahydro furan, 8g lithium aluminium hydride, slowly add 8g 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene, backflow 7h, add 40ml Virahol, 15 milliliter 5% sodium hydroxide successively, filter, steam desolventize, underpressure distillation obtains 5g 2,5-dimethoxy-4 '-ethyl phenyl sulfide ethamine.
Claims (4)
1. 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene, its structural formula is:
2. 2, the method for making of 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene is characterized in that: with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions, uses zinc powder reduction, and underpressure distillation then obtains 2,5-dimethoxy thiophenol; Gained 2,5-dimethoxy thiophenol under 70～80 ℃, alkaline condition with the monobromethane condensation, get yellow oily liquid 2 through underpressure distillation, 5-dimethoxy ethyl phenyl sulfide; 2,5-dimethoxy ethyl phenyl sulfide and phosphorus oxychloride and dimethyl formamide react under 70～80 ℃ of conditions and obtain 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde, gained 2,5-dimethoxy-4 '-ethyl phenyl sulfide formaldehyde obtains 2 with the Nitromethane 99Min. condensation again, 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene.
3. method for making according to claim 2, it is characterized in that: 2,5-dimethoxy benzene sulfonyl chloride makes by following method, ethylene dichloride and terephthaldehyde's ether are mixed stirring and dissolving, be cooled to 0～10 ℃ of following agitation and dropping chlorsulfonic acid and sulfur oxychloride, tell lower floor's oil reservoir, to its distill 2,5-dimethoxy benzene sulfonyl chloride.
4. 2,5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene is used to prepare 2,5-dimethoxy-4 '-ethyl phenyl sulfide ethamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03118594 CN1228320C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03118594 CN1228320C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof |
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| Publication Number | Publication Date |
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| CN1434031A true CN1434031A (en) | 2003-08-06 |
| CN1228320C CN1228320C (en) | 2005-11-23 |
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| CN 03118594 Expired - Fee Related CN1228320C (en) | 2003-02-14 | 2003-02-14 | 2,5-dimethoxy-4-ethyl sulfide-beta-nitrostyrolene and preparation process and use thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103497082A (en) * | 2013-09-24 | 2014-01-08 | 台州学院 | Method for preparing beta-nitrostyrolene and derivatives thereof |
| CN103787936A (en) * | 2014-01-20 | 2014-05-14 | 新发药业有限公司 | Simple synthetic method of trans-p-methylthiocinnamyl alcohol used for industrial production |
| CN108586259A (en) * | 2018-07-09 | 2018-09-28 | 上海华堇生物技术有限责任公司 | A kind of new preparation process of 2- methoxyl groups-beta-nitrostyrene |
-
2003
- 2003-02-14 CN CN 03118594 patent/CN1228320C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103497082A (en) * | 2013-09-24 | 2014-01-08 | 台州学院 | Method for preparing beta-nitrostyrolene and derivatives thereof |
| CN103497082B (en) * | 2013-09-24 | 2015-12-02 | 台州学院 | A kind of method preparing beta-nitrostyrene and derivative thereof |
| CN103787936A (en) * | 2014-01-20 | 2014-05-14 | 新发药业有限公司 | Simple synthetic method of trans-p-methylthiocinnamyl alcohol used for industrial production |
| CN103787936B (en) * | 2014-01-20 | 2016-06-08 | 新发药业有限公司 | A kind of industrialized production is with the trans simple synthesis to first sulfydryl cinnamyl alcohol |
| CN108586259A (en) * | 2018-07-09 | 2018-09-28 | 上海华堇生物技术有限责任公司 | A kind of new preparation process of 2- methoxyl groups-beta-nitrostyrene |
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| Publication number | Publication date |
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| CN1228320C (en) | 2005-11-23 |
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