CN1228320C - 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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- CN1228320C CN1228320C CN 03118594 CN03118594A CN1228320C CN 1228320 C CN1228320 C CN 1228320C CN 03118594 CN03118594 CN 03118594 CN 03118594 A CN03118594 A CN 03118594A CN 1228320 C CN1228320 C CN 1228320C
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- dimethoxy
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- ethyl phenyl
- phenyl sulfide
- nitrostyrolene
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Abstract
The present invention relates to 2, 5-dimethoxy-4-ethyl mercapto group-beta-nitrostyrolene which has a structural formula as the right formula. The present invention also provides a method for manufacturing the compounds. 2, 5-dimethoxythiophenol is obtained by that 2, 5-dimethoxybenzenesulfonyl chloride is taken as raw materials which are restored by zinc powder under the acid condition in 70 to 80 DEG C, then are reduced for pressure and are distilled. The obtained 2, 5-dimethoxythiophenol is condensed with bromoethane under the alkaline condition in 70 to 80 DEG C to obtain the 2, 5-dimethoxybenzene diethyl sulfide by pressure reducing and distilling; the 2, 5-dimethoxy-4-ethyl mercapto group-beta-nitrostyrolene is obtained by that 2, 5-dimethoxybenzenesulfonyl chloride undergo, phosphorus oxychloride and dimethylformamide are reacted under the condition of 70 to 80 DEG C to obtain 2, 5-dimethoxy-4-ethyl mercapto group benzaldehyde, and then the products are condensed with the nitromethane. The 2, 5-dimethoxy-4-ethyl mercapto group-beta-nitrostyrolene prepared by the present invention is used for preparing 2, 5-dimethoxy-4-ethyl mercapto group phenylethylamine.
Description
Technical field
The present invention relates to 2, the method for making of 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene.
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 compound 2, the method for making of 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene.
Technical scheme provided by the invention is: 2, and 5-dimethoxy-4 '-ethylmercapto group-beta-nitrostyrene, its structural formula is
The method for making of above-claimed cpd, with 2,5-dimethoxy benzene sulfonyl chloride is a raw material, under 70～80 ℃, acidic conditions (pH＜1), uses zinc powder reduction, 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 methylene 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 methylene 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 12g2,5-dimethoxy benzene sulfonyl chloride and 18g zinc powder reacted 1 hour down at 80 ℃, and filtration, decompression, steaming are slipped and are obtained 8.2g2,5-dimethoxy thiophenol.
In the 250ml there-necked flask, add 3g potassium hydroxide and 50ml dehydrated alcohol, stirring and dissolving adds 8g2, 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 8g2 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 8g2,5-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 (2)
1. 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 ℃, the condition of pH＜1, uses zinc powder reduction, and underpressure distillation then obtains 2,5-dimethoxy thiophenol; Gained 2,5-dimethoxy thiophenol under 70～80 ℃, the condition of pH＞10 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.
2. method for making according to claim 1, it is characterized in that: 2,5-dimethoxy benzene sulfonyl chloride makes by following method, methylene 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.
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 |
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| 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 CN1434031A (en) | 2003-08-06 |
| CN1228320C true 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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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103497082B (en) * | 2013-09-24 | 2015-12-02 | 台州学院 | A kind of method preparing beta-nitrostyrene and derivative thereof |
| 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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