SU1167184A1 - Method of obtaining 4-h-selenopyrans - Google Patents
Method of obtaining 4-h-selenopyrans Download PDFInfo
- Publication number
- SU1167184A1 SU1167184A1 SU833636934A SU3636934A SU1167184A1 SU 1167184 A1 SU1167184 A1 SU 1167184A1 SU 833636934 A SU833636934 A SU 833636934A SU 3636934 A SU3636934 A SU 3636934A SU 1167184 A1 SU1167184 A1 SU 1167184A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- ether
- triphenyl
- yield
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 229910000058 selane Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-N selane Chemical compound [SeH2] SPVXKVOXSXTJOY-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- MHQSUYHVJQHJAN-UHFFFAOYSA-N 2,4,6-triphenyl-4h-selenopyran Chemical compound [Se]1C(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MHQSUYHVJQHJAN-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KMDRTMGEOUIDDZ-UHFFFAOYSA-N 4h-selenopyran Chemical compound C1C=C[Se]C=C1 KMDRTMGEOUIDDZ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
СПОСОБ ПОЛУЧЕНИЯ 4-Н-СЕЛЕНОПИРАНОВ общей формулы CftH/tR бН|- 0 -СеНв где R - Н или ОСИ,-группа, путем взаимодействи раствора 1,3,5-трифенил- или 1,5-дифенил-3-METHOD OF OBTAINING 4-H-SELENOPIRANES of the general formula CftH / tR bN | - 0 -SeHB where R is H or OSI, is a group, by reacting a solution of 1,3,5-triphenyl or 1,5-diphenyl-3-
Description
Изобретение относитс к улучшен му способу получени 4-Н-селенопир нов общей формулы С-вНдК где или OCHj группа, представл ющие интерес в качестве лупродуктов при синтезе лекарствен ных веществ, красителей и средств зал(иты растений, компонентов при создании фотогальванических элемен тов. Целью изобретени вл етс увел чение выхода и расширение ассортим та целевых продуктов путем увеличе растворимости реагентов. Изобретение иллюстрируетс следующими примерами. Пример 1. 2,4,6-трифенил-4-Н-селенопиран . 50 МП 5 и. раствора НС 1 в абсо лютном метаноле в атмосфере аргона насьпцают селеноводородом и в течение 1 ч прикапывают раствор 3,28 г (0,01 моль) 1,3,5-трифенил-пентадио Ha-ljS в 5 МП сухого хлороформа, после чего, не прекраща тока селеноводорода , перемешивают еще 5 ч, поддержива температуру реакционной смеси IS-IT C. Выпавший осадок отфильтровывают, промывают абсолютным метанолом 2-5 мп, сушат, раство р ют в эфире и пропускают через колонку с AljOj (3-10 см) элюент эфир дл удалени элементарного селена , получают 3,32 г (89,1%) 4-Н-селенопирана , Маточньш раствор разбавл ют эфиром и тщательно промы вают водой, сушат, эфир упаривают, выделившеес масло дел т на колонке с Al20j элюент - гексан:эфир - 4:1 Общий выход 3,47 г (93%). Т.пл.107109 С . Вычислено, %: С 74,0; Н 4,9. Cjg Найдено, %: С 74,2 Н 4,8. ШР-спектр ССЦСС Д) м.д. 6.11 (Д, 2Н); 4,19 (Т, 1Н) 7,05-7,52 (М, 15Н). Пример 2. 2,4,6-трифенил-А-Н-селенопиран . Провод т аналогично примеру 1, использу 3,2 Н. раствор НС1 в мета ноле. Выход 87%, т. пл. 107-109 0, проба смешени с Достоверным образцом депрессии т. пл. не дала. П р и м е р 3. 2,4,6-трифенил-4-Н-селенопиран . Синтез провод т аналогично примеру 1, использу 3,8 Н. раствор НС1 в метаноле и увеличива врем реакции до 8 ч. Выход 88%. Т.пл. 107,5109°С , проба смешени с достоверным образцом депрессии т. пл. не дала. Пример 4. 2,4,6-трифенил-4-Н-селенопиран . Синтез провод т аналогично примеру 1 , использу 2,2 Н. раствор НС1 в метаноле. Получают после обработки масл нистый продукт, После предварительной очистки выход целевого продукта составл ет 50%. Выход хроматографически чистого селенопирана 16%. Т.пл. 107-109 с, проба смешени с достоверным образцом депрессии т. пл, не дала. Пример 5. 2,4,6-трифенил-4-Н-селенопиран . Синтез провод т аналогично примеру 1, использу 6 Н. раствор НС1 в метаноле. Выход 85%. Усиленный ток HjSe ввиду легкости разложени последнего необходим дл проведени реакции. Т. пл. 106-108 С, проба смешени с достоверным образцом депрессии т. пл. не дала. Пример 6. 2,6-дифенил-4- (п-метоксифенил)-4-Н-селенопиран. 40 мл ,5 Н. раствора НС1 в абсолютном метаноле в атмосфере аргона насьш;ают селеноводородом и в течение 30 мин прикапывают раствор 2,87 г (0,008 моль) 1,5-дифeнил-3-(n-мeтoкcифeнил )-пeнaтдиo нa-1 , 5 в 6 мл сухого хлороформа, после чего, не прекраща тока селеноводорода, размешивают еще 6ч, поддержива температуру реакционной смеси 15-17°С.. Выпавший осадок отфильтровывают, промывают метанолом, сушат, раствор ют в эфире и пропускают через колонку с AljOj размером ЗЮ см (элюент - эфир). Получают 2,59 г (80%) целевого продукта. Маточный раствор разбавл ют эфиром и тщательно промывают дистиллированной водой, сушат, эфир упаривают, выделившеес масло дел т на колонке с AljOj (элюент - гексан: .эфир - 4:1), общий выход 2,78 г (86%). Т. пл. 104-105 0.The invention relates to an improved method for the preparation of 4-H-selenopropy of the general formula C-vDd where or OCHj group, which are of interest as loops in the synthesis of medicinal substances, dyes and gels (plants and components when creating photovoltaic cells. The aim of the invention is to increase the yield and the expansion of the assortment of target products by increasing the solubility of the reagents.The invention is illustrated by the following examples: Example 1. 2,4,6-triphenyl-4-H-selenopyran 50 MP 5 and HC 1 solution in abs. lute met in an atmosphere of argon, hydrogen sulfide is saturated with hydrogen sulfide and a solution of 3.28 g (0.01 mol) of 1,3,5-triphenyl pentadio Ha-1jS in 5 MP of dry chloroform is added dropwise for 1 h, after which, without stopping the flow of hydrogen selenide, they are stirred for another 5 hours, maintaining the temperature of the IS-IT C reaction mixture. The precipitated precipitate is filtered, washed with absolute methanol 2-5 mp, dried, dissolved in ether and passed through a column of AljOj (3-10 cm) ether to remove elemental selenium , 3.32 g (89.1%) of 4-H-selenopyran is obtained. The mother solution is diluted with ether and washed well. with water, dried, the ether was evaporated, the separated oil was divided column Al20j eluent - hexane: ether - 4: 1 Overall yield 3.47 g (93%). Mp.107109 c. Calculated,%: C 74.0; H 4.9. Cjg Found: C: 74.2 H 4.8. WSS-spectrum SSSSS D) ppm 6.11 (D, 2H); 4.19 (T, 1H) 7.05-7.52 (M, 15H). Example 2. 2,4,6-triphenyl-AH-selenopyran. It is carried out as in Example 1, using 3.2 N. A solution of HCl in methanol. Exit 87%, so pl. 107-109 0, mixing test with a reliable sample of depression t. Pl. not given. PRI me R 3. 2,4,6-triphenyl-4-H-selenopyran. The synthesis is carried out analogously to example 1, using a 3.8 N. solution of HCl in methanol and increasing the reaction time to 8 hours. Yield 88%. M.p. 107.5109 ° C, mixing sample with a reliable sample of depression, m. Pl. not given. Example 4. 2,4,6-triphenyl-4-H-selenopyran. The synthesis is carried out analogously to example 1, using 2.2 N. A solution of HCl in methanol. After treatment, an oily product is obtained. After preliminary purification, the yield of the target product is 50%. The yield of chromatographically pure selenopyran is 16%. M.p. 107-109 s, the mixing test with a reliable sample of depression, t. Pl, did not give. Example 5. 2,4,6-triphenyl-4-H-selenopyran. The synthesis is carried out analogously to Example 1, using 6 N. A solution of HCl in methanol. Yield 85%. The increased current HjSe, due to the ease of decomposition of the latter, is necessary for carrying out the reaction. T. pl. 106-108 ° C, mixing test with a reliable sample of depression t. Pl. not given. Example 6. 2,6-diphenyl-4- (p-methoxyphenyl) -4-H-selenopyran. 40 ml, 5 N. solution of HCl in absolute methanol in an argon atmosphere; see that there is hydrogen selenium and a solution of 2.87 g (0.008 mol) of 1,5-difenil-3- (n-methoxyphenyl) -penoate 1, 5 in 6 ml of dry chloroform, after which, without discontinuing the hydrogen sulfide, stir for another 6 hours, maintaining the temperature of the reaction mixture at 15-17 ° C. The precipitated precipitate is filtered, washed with methanol, dried, dissolved in ether and passed through a column AljOj size ZU cm (eluent - ether). 2.59 g (80%) of the desired product are obtained. The mother liquor is diluted with ether and washed thoroughly with distilled water, dried, the ether is evaporated, the separated oil is divided on a column with AljOj (eluent is hexane: ether: 4: 1), the total yield is 2.78 g (86%). T. pl. 104-105 0.
311671844311671844
Вычислено, %: С 71,5;Н 5,0.Пример 7. Синтез провод тCalculated,%: C 71.5; H 5.0. Example 7. Synthesis is carried out
024 20 0аналогично примеру 1 при . Выход024 20 Same as Example 1 at. Output
Найдено, %: С 71,7, Н5,3.достигает 71%.Found,%: C 71.7, H5.3. Reaches 71%.
roiP-спектр ОС Ц()м.д. 3,75Пример 8. Синтез провод тOS roiP-spectrum () ppm 3.75 Example 8. Synthesis is carried out
(С , ЗН), 4,16 (Т.1Н), 6,11 (Д, 2Н), 5 ан огично примеру 1 при . Выход(C, 3N), 4.16 (T. 1H), 6.11 (D, 2H), 5 in addition to Example 1 at. Output
6,73-6,53 (Н 14Н).Достигает 7.5%.6.73-6.53 (H 14H). Reaches 7.5%.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU833636934A SU1167184A1 (en) | 1983-06-29 | 1983-06-29 | Method of obtaining 4-h-selenopyrans |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU833636934A SU1167184A1 (en) | 1983-06-29 | 1983-06-29 | Method of obtaining 4-h-selenopyrans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1167184A1 true SU1167184A1 (en) | 1985-07-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833636934A SU1167184A1 (en) | 1983-06-29 | 1983-06-29 | Method of obtaining 4-h-selenopyrans |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1167184A1 (en) |
-
1983
- 1983-06-29 SU SU833636934A patent/SU1167184A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Degani L., Vincengi С., Poll Sci Fac. Chera. Bologna. 1967, 25, p. 51-60. Харченко В.Г., Древко. Б,И. Реакции дикетонов с селеноводородом. ЖОХ, 1982., № 18, f 12, с. 2595. * |
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