SU52430A1 - The method of obtaining salts of alkyl-sulfuric acid N, N'-alkyl diacridyl-9-urea - Google Patents
The method of obtaining salts of alkyl-sulfuric acid N, N'-alkyl diacridyl-9-ureaInfo
- Publication number
- SU52430A1 SU52430A1 SU52430A1 SU 52430 A1 SU52430 A1 SU 52430A1 SU 52430 A1 SU52430 A1 SU 52430A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- urea
- diacridyl
- sulfuric acid
- obtaining salts
- Prior art date
Links
- 239000004202 carbamide Substances 0.000 title description 10
- 150000003839 salts Chemical class 0.000 title description 5
- 239000011780 sodium chloride Substances 0.000 title description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- XJGFWWJLMVZSIG-UHFFFAOYSA-N 9-Aminoacridine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=NC2=C1 XJGFWWJLMVZSIG-UHFFFAOYSA-N 0.000 description 4
- 229960001441 aminoacridine Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(chloroethyl) ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- ZFGUOIRBIJBHNF-UHFFFAOYSA-N C1(=CC=CC2=NC3=CC=CC=C3C=C12)NC(=O)OCC Chemical compound C1(=CC=CC2=NC3=CC=CC=C3C=C12)NC(=O)OCC ZFGUOIRBIJBHNF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- -1 alkyl sulfuric acid Chemical compound 0.000 description 1
- 229940027998 antiseptics and disinfectants Acridine derivatives Drugs 0.000 description 1
- 238000005039 chemical industry Methods 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZCWORVFRBDQDX-UHFFFAOYSA-N ethyl N-acridin-9-ylcarbamate Chemical compound C1=CC=C2C(NC(=O)OCC)=C(C=CC=C3)C3=NC2=C1 WZCWORVFRBDQDX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
За последние годы производные акридина приобрели большое значение в химико-фармацевтической промышленности . В св зи с этим не лишены интереса синтезы новых препаратов , проводимые в этом р ду гетероциклических соединений, так как современем многие из них могут оказатьс практически ценными.In recent years, acridine derivatives have acquired great importance in the chemical and pharmaceutical industry. In this connection, the synthesis of new preparations carried out in this series of heterocyclic compounds is not without interest, since many of them can be practically valuable today.
Явторами насто щего изобретени предлагаетс новый метод синтеза солей алкилосерной кислоты N.N алкилдиакридил-9-мочевины . Этот способ состоит в том, что сначала получают акридил-9-уретан путем воздействи хлоругольного эфира на 9-аминоакридин . Акридил-уретан при нагревании с 9-аминоакридином в подход щем растворителе дает M.N-диакридил-9-мочевину , котора при обработке диарилсульфатом образует соли алкилосерной кислоты IS.N - алкилдиакридил-9-мочевины .The authors of the present invention propose a new method for the synthesis of salts of alkylsulfuric acid N.N alkyl diacridyl-9-urea. This method consists in first obtaining acridyl-9-urethane by the action of chloro-ester on 9-amino-acridine. Acridyl-urethane, when heated with 9-amino-acridine in a suitable solvent, gives M.N-diacridyl-9-urea, which, when treated with diarylsulfate, forms alkyl.Isulfonic acid salts. IS.N is alkyl diacridyl-9-urea.
Предлагаемый метод иллюстрируетс следующими примерами:The proposed method is illustrated by the following examples:
Пример. К нагретому до 150° раствору 9 г 2-метокси-б-хлор-9-аминоакридина в 80 см нитробензола прибавл ют 4 г хлоругольного эфира. Смесь нагревают на масл ной бане при 110-120 в течение 3 часов. Гор чий раствор фильтруют, при сто нии из фильтрата выкристаллизовываетс 2-метокси-б-хлоракридил-9-уретан , который после кристаллизации из спирта плавитс при 209°.Example. To a solution of 9 g of 2-methoxy-b-chloro-9-amino-acridine in 80 cm of nitrobenzene, heated to 150 ° C, is added 4 g of chloroethyl ether. The mixture is heated in an oil bath at 110-120 for 3 hours. The hot solution is filtered, and 2-methoxy-b-chloroacridyl-9-urethane crystallizes out from the filtrate, which, after crystallization from alcohol, melts at 209 °.
В колбу Вюрца помещают 5 г 2метокси-6-хлоракридил-9-уретана , 4 г 2-метокси-б-хлор-9-аминоакридина и 20 см нитробензола. Смесь нагревают на масл ной бане при 130-160° в течение 3 часов. Выпавший осадок отфильтровывают , промывают водным пинолином, спиртом и эфиром. Полученна N.N-ди (2 метокси-б-хлоракридил )-9-мочевина плавитс с разложением при 275.In a flask Wurtz placed 5 g of 2methoxy-6-chloroacridyl-9-urethane, 4 g of 2-methoxy-b-chloro-9-amino-acridine and 20 cm of nitrobenzene. The mixture is heated in an oil bath at 130-160 ° for 3 hours. The precipitation is filtered off, washed with aqueous pinolin, alcohol and ether. The resulting N.N-di (2 methoxy-b-chloroacridyl) -9-urea melts with decomposition at 275.
0,6 г M.N-ди (2-метокси-б-хлоракридил )-9-мочевины, 30 см нитробензола и 0,18 г диметилсульфата нагревают до 150°. По охлаждении выпадают кристаллы N.N - метилсульфометилата ди - (2-метокси-б-хлоракридил)-9мочевины , которые после кристаллизации из воды плав тс с разложением при 255°.0.6 g of M.N-di (2-methoxy-b-chloroacridyl) -9-urea, 30 cm of nitrobenzene and 0.18 g of dimethyl sulfate are heated to 150 °. Upon cooling, N.N-methyl sulfomethylate di- (2-methoxy-b-chloroacridyl) -9 urea crystals precipitate, which after crystallization from water melts with decomposition at 255 °.
Предмет изобретени .The subject matter of the invention.
Способ получени солей алкилосерной кислоты N.N - алкилдиакридил-9-мочевины , отличающийс тем, что на раствор 9-аминоакридина или его производного в каком-либо органическом растворителе действуют при нагревании хлороугольным эфиром, выпавший 9-акридилуретан отфильтровывают и обрабатывают при нагревании ВТОМ же растворителе 9-аминоакридном или его производными, - полученную Ы.К-диакридил-9-мочевину отдел ют и обрабатывают в тех же услови х диарилсульфатом с целью получени соли алкилосерной кислоты Ы.Ы-алкилдиакридил-9-мочевины, которую и отдел ют от реакционной массы обычными приемами.The method of producing alkylnosulfuric acid salts of NN - alkyl diacridyl-9-urea, characterized in that a solution of 9-amino-acridine or its derivative in some organic solvent is acted upon by heating with chloroform ether, the precipitated 9-acridylurethane is filtered and treated by heating with WTO same solvent 9 -aminoacridine or its derivatives, obtained by LK-diacridyl-9-urea, is separated and treated under the same conditions with diarylsulfate in order to obtain the salt of alkyl sulfuric acid LY-alkyl diacridyl-9-urea, and was separated from the reaction mixture by conventional means.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10774047B2 (en) * | 2015-04-17 | 2020-09-15 | The Trustees Of The University Of Pennsylvania | Dimeric quinacrine derivatives as autophagy inhibitors for cancer therapy |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10774047B2 (en) * | 2015-04-17 | 2020-09-15 | The Trustees Of The University Of Pennsylvania | Dimeric quinacrine derivatives as autophagy inhibitors for cancer therapy |
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