SU252330A1 - METHOD OF OBTAINING OXYMES - Google Patents
METHOD OF OBTAINING OXYMESInfo
- Publication number
- SU252330A1 SU252330A1 SU1256900A SU1256900A SU252330A1 SU 252330 A1 SU252330 A1 SU 252330A1 SU 1256900 A SU1256900 A SU 1256900A SU 1256900 A SU1256900 A SU 1256900A SU 252330 A1 SU252330 A1 SU 252330A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxymes
- obtaining
- dialkylsulfonium
- acetonyl
- dry
- Prior art date
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 3
- -1 acetonyldimethylsulfonium bromide Chemical compound 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области . ОКСИМОВ ацетонилдиалкилсульфонийбромидов, которые могут найти применение как физиологически активные вещества.The invention relates to the field. OXYMES acetonyl dialkylsulfonium bromides, which can be used as physiologically active substances.
В литературе отсутствуют данные о синтезе ОКСИМОВ, содержащих в молекуле -сульфониевую icepy. Новые соединени получают оксимированием ацетонилдиалкилсульфонийбромидов гидроксиламином в метиловом спирте по схемеIn the literature, there are no data on the synthesis of oximes containing icepy sulfonium in the molecule. The new compounds are prepared by oximation of acetonyl dialkylsulfonium bromides with hydroxylamine in methyl alcohol according to the scheme
R.R.
S-СН2-с-CHjS-CH2-c-CHj
Br+NH,OH-Br + NH, OH-
//
CH,-C-CH, CH, -C-CH,
Br+НаО. II NOHBr + NaO. II NOH
Пример. К 9,8 г (0,049 моль) ацетонилдиметилсульфонийбромида прибавл ют раствор в метиловом спирте 0,052 моль гпдроксиламина основани (из 3,62 г NhbOH НС1 и 2,92 г ) и оставл ют при комнатнойExample. To 9.8 g (0.049 mol) of acetonyldimethylsulfonium bromide, add a solution in methyl alcohol of 0.052 mol of gproxylamine base (from 3.62 g of NhbOH HCl and 2.92 g) and leave it at room temperature.
температуре на 18 час. Метиловый спирт упаривают под вакуумом водоструйного насоса без нагрева. Остаток - густую жидкость раствор ют в смесп 5 мл абсолютного этиловогоtemperature for 18 hours Methyl alcohol is evaporated under vacuum of a water-jet pump without heating. Residue - a thick liquid is dissolved in a mixture of 5 ml of absolute ethyl
спирта п 10 мл сухого хлороформа; дл высушпвани засыпают 20 г прокаленного сульфата натри и оставл ют до следующего дн . Сульфат натри отсасывают, промывают абсолютным этиловым спиртом, ф 1льтратalcohol n 10 ml of dry chloroform; 20 g of calcined sodium sulfate are poured for drying and left to the next day. Sodium sulfate is sucked off, washed with absolute ethyl alcohol, 1ltrat
упарпвают под вакуумом до получени густой жидкости. Дл удалени из нее остатков растворителей и исходных веществ тщательно взбалтывают жидкость с порци ми сухого этилацетата по 7-10 мл (3 раза) и сухогоBoil down under vacuum to obtain a thick liquid. To remove residual solvents and starting materials from it, carefully stir up the liquid with portions of dry ethyl acetate 7-10 ml (3 times) and dry
ацетона (3 раза), растворптели декантируют. Па остаток наслаивают 5 мл сухого этилацетата и оставл ют в испарителе холодильника кристаллизоватьс . Осадок отсасывают, промывают смесью сухой этилацетат-абсолютн з1Й этанол (1 : 1), сущат в вакуум-эксикаторе . Выход 4,1 г. Кристаллизуют из абсолютного этилового спирта.acetone (3 times), the solution was decanted. The residue was layered with 5 ml of dry ethyl acetate and left to crystallize in the evaporator of the refrigerator. The precipitate is filtered off with suction, washed with a mixture of dry ethyl acetate-absolute ethanol (1: 1), and is concentrated in a vacuum desiccator. Yield 4.1 g. Crystallized from absolute ethanol.
Аналогично получают другие оксимы ацетонилдиалкилсульфонийбромидов , приведенныеSimilarly, other acetonyl dialkylsulfonium bromide oximes are obtained, given
в таблице.in the table.
Оксимы ацетонилдналки.чсульфонийбромидоаOximes acetonyldnalki.chsulfoniybromidoa
(СНз-С-СН,-S/ ) Вг/R(CHS-C-CH, -S /) Br / R
П р н м е ч а к и с. Температуры плавлени определены на APPROACH Melting points are determined by
Предмет изобретени Subject invention
Способ получени оксимов ацетонилдиалкилсульфоиийбромидов общей формулыThe method of producing oxime acetonyl dialkylsulfoium ybromides of the general formula
NOHNOH
5-СН„-С-СНэ5-CH „-C-SNE
Вг,Vg,
LRгде R означает низший алкил, отличающийс тем, что ацетоиилдиалкилсульфолийбромпд подвергают взаимодействию со спиртовьш раствором тндроксиламииа осиоваии с последующи выделением целево1о иродукта известиыми приемами. микроиагревателыюм столике Кофлера.LR wherein R is lower alkyl, characterized in that acetoyl dialkylsulfonium bromide is reacted with an alcohol solution of tndroxylamine and osovaia followed by isolation of the target product by lime techniques. Kofler's micro-table.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU252330A1 true SU252330A1 (en) |
Family
ID=
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