SU1313856A1 - Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 - Google Patents
Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 Download PDFInfo
- Publication number
- SU1313856A1 SU1313856A1 SU853963771A SU3963771A SU1313856A1 SU 1313856 A1 SU1313856 A1 SU 1313856A1 SU 853963771 A SU853963771 A SU 853963771A SU 3963771 A SU3963771 A SU 3963771A SU 1313856 A1 SU1313856 A1 SU 1313856A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- trans
- cis
- crown
- diaminodibenzoyl
- substituted
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 12
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 101100404726 Arabidopsis thaliana NHX7 gene Proteins 0.000 claims 1
- 102000057028 SOS1 Human genes 0.000 claims 1
- 108700022176 SOS1 Proteins 0.000 claims 1
- 101100197320 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RPL35A gene Proteins 0.000 claims 1
- 101150100839 Sos1 gene Proteins 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 2
- 150000003983 crown ethers Chemical class 0.000 abstract 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical class O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Изобретение касаетс замещенных краунэфиров, в частности ЦИС- или транс-диаминодибензоилди- бензо-18-кразпн-6, которые могут быть замещены в бензоильной группе галогеном или низшим алкилом - промежуточных продуктов дл синтеза биологически активных веществ. Цель - J разработка нового способа получени ценных краунэфиров. Синтез последних ведут из соответствующего замещенного бензоилхлорида с цис- или транс-диаминодибензо-18-краун- -6 в среде органического растворител в присутствии ZnCl-jr. при IIO-UO C, лучше 120-130 С. Способ обеспечивает высокий выход (до 70%) ценных краунэфиров .из доступных исходных веществ. I з.п. ф-лы, 1 табл. о $The invention relates to substituted crown ethers, in particular, CIS or trans-diaminodibenzoyl-benzo-18-krazpn-6, which can be substituted in the benzoyl group by halogen or lower alkyl, intermediate products for the synthesis of biologically active substances. Objective - J to develop a new method for obtaining valuable crown ethers. The latter are synthesized from the corresponding substituted benzoyl chloride with cis- or trans-diaminodibenzo-18-crown-6 in an organic solvent medium in the presence of ZnCl-jr. with IIO-UO C, better than 120-130 C. The method provides a high yield (up to 70%) of valuable crown ethers from available starting materials. I zp f-ly, 1 tab. about $
Description
113113
Изобретение относитс к новому способу получени производных цис- или транс-диаминодибензоилдибензо- -18-краун-6, которые могут найти применение в качестве промежуточных соединений дл получени биологически активных веществ.This invention relates to a novel process for the preparation of cis or trans diaminodibenzoyl dibenzo-18-crown-6 derivatives, which can be used as intermediates for the preparation of biologically active substances.
Цель изобретени - разработка нового способа.The purpose of the invention is to develop a new method.
Способ иллюстрируетс следующим примером,The method is illustrated by the following example.
П р и м. е р. Смесь 3,9 г транс- -диаминодибензо-18- краун-6 и 7 мл бензоилхлорида в абсолютном декане нагревают при перемешивании до и добавл ют б г безводного хлористого цинка. Реакционную смесь перемешивают при 125 С в течение часа. Затем осторожно добавл ют избыток воды водный раствор сливают, осадок нагревают с 72%-ным . в течение получаса при температуре кипени раствора . Реакционную смесь выливают на лед, водным аммиаком устанавливают щелочную среду, отфильтровьшают выпавший осадок и сушат на воздухе. Продукт перекристаллизовьшают из метанола и бензола. Выход 68%, 4 г.PRI m. A mixture of 3.9 g of trans-α-diaminodibenzo-18-crown-6 and 7 ml of benzoyl chloride in absolute decane is heated with stirring before and b g of anhydrous zinc chloride is added. The reaction mixture was stirred at 125 ° C for one hour. Then, an excess of water is carefully added, the aqueous solution is drained, the precipitate is heated with 72%. within half an hour at the boiling point of the solution. The reaction mixture is poured onto ice, the alkaline medium is established with aqueous ammonia, the precipitated precipitate is filtered off and dried in air. The product is recrystallized from methanol and benzene. Yield 68%, 4 g.
Сведени о режимах осуществлени способа приведены в таблице.Details of the modes of implementation of the method are shown in the table.
Процесс осуществл ют в среде инертного органического растворител декана (примеры 1-12 таблицьО и нитробензола (примеры 15-17, таблицы) при ПО-140 С,The process is carried out in an environment of an inert organic solvent of decane (examples 1-12 of table O and nitrobenzene (examples 15-17, tables) with PO-140 C,
Оптимальной температурой процесса вл етс 120-130°С. При отклонении на 10°С от данного интервала выход целевых продуктов резко снижаетс .The optimum process temperature is 120-130 ° C. With a deviation of 10 ° C from this interval, the yield of the target products sharply decreases.
3856238562
Таким образом, предлагаемый способ позвол ет получать производные цис- и транс-диаминодибензоилдибен -18-краун-6 с высокими выходами,Thus, the proposed method allows to obtain cis- and trans-diaminodibenzoyl-diben-18-crown-6 derivatives with high yields,
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853963771A SU1313856A1 (en) | 1985-10-05 | 1985-10-05 | Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU853963771A SU1313856A1 (en) | 1985-10-05 | 1985-10-05 | Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1313856A1 true SU1313856A1 (en) | 1987-05-30 |
Family
ID=21200887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853963771A SU1313856A1 (en) | 1985-10-05 | 1985-10-05 | Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1313856A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5142068A (en) * | 1989-10-06 | 1992-08-25 | Virginia Tech Intellectual Properties, Inc. | Mono- and di(functionally-substituted phenylene) semi-rigid crowns and processes for making |
| WO1992018495A1 (en) * | 1991-04-16 | 1992-10-29 | Virginia Tech Intellectual Properties, Inc. | Novel dibenzo crown monomers and polymers formed therefrom |
-
1985
- 1985-10-05 SU SU853963771A patent/SU1313856A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 4104275, кл. С 07 D 323/00, 1978. D. АО Walsh.-The synthesis of 2-aminobenzophenones. - Synthesis. 1980, p. 677. Иванов Э. И. и др. Синтез макро- циклических производных 1,4-бензди- азепина и хиназолина. - РЖ Хими , 1985, 2Ж 282 Деп. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5142068A (en) * | 1989-10-06 | 1992-08-25 | Virginia Tech Intellectual Properties, Inc. | Mono- and di(functionally-substituted phenylene) semi-rigid crowns and processes for making |
| US5302729A (en) * | 1989-10-06 | 1994-04-12 | Virginia Tech Intellectual Properties, Inc. | Dibenzo crown monomers and polymers formed therefrom |
| WO1992018495A1 (en) * | 1991-04-16 | 1992-10-29 | Virginia Tech Intellectual Properties, Inc. | Novel dibenzo crown monomers and polymers formed therefrom |
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