SU345152A1 - METHOD OF OBTAINING Aryl (Alkyl) Alkynyl Selenides - Google Patents
METHOD OF OBTAINING Aryl (Alkyl) Alkynyl SelenidesInfo
- Publication number
- SU345152A1 SU345152A1 SU1445713A SU1445713A SU345152A1 SU 345152 A1 SU345152 A1 SU 345152A1 SU 1445713 A SU1445713 A SU 1445713A SU 1445713 A SU1445713 A SU 1445713A SU 345152 A1 SU345152 A1 SU 345152A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- selenides
- alkynyl
- aryl
- obtaining aryl
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title description 6
- 125000003118 aryl group Chemical group 0.000 title description 5
- -1 Alkynyl Selenides Chemical class 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к получению новых, не описанных в литературе этиниловых селеиидов , которые могут найти применение в народном хоз йстве. В литературе описан способ получени алкинильных селенидов, заключающийс во взаимодействии селена с ацетиленидом натри в жидком аммиаке, с последующим действием галоидных алкилов. Недостатком указанного способа вл етс невозможность получени арилалкииилселенидов и необходимость проведени процесса в жидком аммиаке. С целью получени указанных соединений предлагаетс способ получени арил(алкил)алкицилселенидов общей формулы - , где R, R- арил или алкил. Способ заключаетс во взаимодействии селенол та натри с 1-галоидалкилом в растворителе , например диметилформамиде, с последующим выделением целевого продукта. Предлагаемый способ отличаетс м гкостью условий проведени реакции и обеспечивает хороший выход (60-757о) целевых продуктов . Пример I. Способ получени 1-фенил-2п-хлорфенилселеноэтина . реакционную массу разбавл ют водой, органический слой извлекают эфиром. Растворитель отгон ют, остаток перекристаллизовывают из метанола. Получено 2,95 (72%) 1-фенил-2-/г-хлорфенилселеноэтина . Т. пл. 47°С. Найдено, %: С 57,50; Н 3,15. CnHsClSe. Вычислено, %: С 57,66; Н 3,11. Пример 2. Способ получени 1-фенил-2 -толилселеноэтина . В услови х примера 1 к раствору 3 г /;-селенокрезол та натрн в 60 .ил диметилформамида прибавл ют 2,9 г 1-бром-2-фенилэтина. Получено 2,76 г (65%) 1-фенил-2-«-толилселеноэтина. Т. пл. 50- 50 5°С Найдено, %: С 66,71; Н 4,45. CjsHioSe. Вычислено, %: С 55,42; Н 4,46. Предмет изобретени Способ получени арил (алкил)алкиннлселенидов общей формулы , где R,R - арил или алкил, отличающийс те.м, что селенол т натри подвергают взаимодействию с 1-галоидалкилом в растворителе, папример , диметилформамиде, с последующим выделением целевого продукта известным способом .The invention relates to the preparation of new ethynyl seleides that are not described in the literature, which can be used in the national household. The literature describes a process for the preparation of alkynyl selenides, which consists in the interaction of selenium with sodium acetylenide in liquid ammonia, followed by the action of halide alkyls. The disadvantage of this method is the impossibility of obtaining arylalkyl and selenides and the need to carry out the process in liquid ammonia. In order to obtain these compounds, a method for the preparation of aryl (alkyl) alkyl acylenides of the general formula - where R, R is aryl or alkyl is proposed. The method involves reacting sodium selenolate with 1-haloalkyl in a solvent, for example dimethylformamide, followed by isolation of the desired product. The proposed method differs in the softness of the reaction conditions and provides a good yield (60-757 °) of the desired products. Example I. The method of producing 1-phenyl-2n-chlorophenylselenoetin. the reaction mass is diluted with water, the organic layer is extracted with ether. The solvent is distilled off, the residue is recrystallized from methanol. 2.95 (72%) 1-phenyl-2- / g-chlorophenylselenoetin was obtained. T. pl. 47 ° C. Found,%: C 57.50; H 3.15. CnHsClSe. Calculated,%: C 57.66; H 3.11. Example 2. A method for the preparation of 1-phenyl-2-tolyl selenoetin. Under the conditions of Example 1, 2.9 g of 1-bromo-2-phenylethine was added to a solution of 3 g /; - selenocresol and soda in 60 ml of dimethylformamide. 2.76 g (65%) of 1-phenyl-2 - “- tolylselenoetin was obtained. T. pl. 50- 50 5 ° C Found,%: C 66.71; H 4.45. CjsHioSe. Calculated,%: C 55.42; H 4.46. The subject of the invention. Method for the preparation of aryl (alkyl) alkynlelenides of the general formula where R, R is aryl or alkyl, differing in that sodium selenolate is reacted with 1-haloalkyl in a solvent, for example dimethylformamide, followed by isolation of the target product in a known manner .
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU345152A1 true SU345152A1 (en) |
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