DD201306A1 - PROCESS FOR THE PREPARATION OF 5-ACYL-3-ARYL-2-DIALKYLAMINOTHIOPHENESE - Google Patents
PROCESS FOR THE PREPARATION OF 5-ACYL-3-ARYL-2-DIALKYLAMINOTHIOPHENESE Download PDFInfo
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- DD201306A1 DD201306A1 DD23561781A DD23561781A DD201306A1 DD 201306 A1 DD201306 A1 DD 201306A1 DD 23561781 A DD23561781 A DD 23561781A DD 23561781 A DD23561781 A DD 23561781A DD 201306 A1 DD201306 A1 DD 201306A1
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Abstract
Derartige Verbindungen koennen Bedeutung fuer die Herstellung biologisch wirksamer Praeparate erlangen. Mit der Erfindung soll errreicht werden, die bisher unbekannten 5-Acyl-3-aryl-2-dialkylthiophene in einfacher Weise herzustellen. Dies geschieht erfindungsgemaess in der Weise, dass substituierte 3-Hydroxythioacrylamide mit Halogenmethylenverbindungen gegebenenfalls in Gegenwart einer Base zu den 5-Acyl-3-aryl-2-dialkyl-aminothiophenen des Typs I umgesetzt werden. Die Erfindung ist in der chemischen und pharmazeutischen Industrie einsetzbar. Formel ISuch compounds can gain importance for the production of biologically active preparations. The invention seeks to achieve the previously unknown 5-acyl-3-aryl-2-dialkylthiophenes in a simple manner. This is done according to the invention in such a way that substituted 3-hydroxythioacrylamides are reacted with halomethylene compounds, if appropriate in the presence of a base, to give the 5-acyl-3-aryl-2-dialkylaminothiophenes of type I. The invention can be used in the chemical and pharmaceutical industries. Formula I
Description
2 356 17 32 356 17 3
Verfahren zur Herstellung von ^- thibphenenProcess for the preparation of --thibphenes
Int.01. CO?D 333/20 Anwendungsgebiet der ErfindungInt.01. CO D 333/20 Field of application of the invention
Die Erfindung betrifft ein Verfahren zur Herstellung vonThe invention relates to a process for the preparation of
5-Acyl-3~aryl-2-dialkylaminothiophenen.5-Acyl-3 ~ aryl-2-dialkylaminothiophenen.
Derartige Verbindungen können Bedeutung für die HerstellungSuch compounds may be important for the preparation
biologisch wirksamer Präparate erlangen.obtain biologically effective preparations.
Charakteristik der bekannten technischen Lösungen i 5-Acyl-3-a3?yl-2-dialkylaminothiophene sind bisher unbekannt. Ziel der ErfindungCharacteristic of the Known Technical Solutions i 5-Acyl-3-a3-yl-2-dialkylaminothiophenes are hitherto unknown. Object of the invention
Ziel der Erfindung ist es, die bisher unbekannten 5-Acyl-3-aryl-2-dialkylaminothiophene zugänglich zu machen. 'The aim of the invention is to make the hitherto unknown 5-acyl-3-aryl-2-dialkylaminothiophenes accessible. '
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
Aufgabe der Erfindung ist" es, ein einfaches Verfahren zur Herstellung von 5-Acyl~3-aryl-2-dialkylaminothiophenen zu entwickeln. The object of the invention is to develop a simple process for the preparation of 5-acyl-3-aryl-2-dialkylaminothiophenes.
Erfindungsgemäß wird diese Aufgabe dadurch gelöst, daß ein substituiertes 3-Hydroxythioacrylamid des Typs. IAccording to the invention, this object is achieved in that a substituted 3-hydroxythioacrylamide of the type. I
HO-OH=C-C=S IHO-OH = C-C = S I
- NR2R5 - NR 2 R 5
mit einer Halogenmethylenverbindung des Typs IIwith a type II halomethylene compound
235617 3235617 3
HalCH2-p(-R IIHalCH 2 -p ( -R II
gegebenenfalls in Gegenwart einer Base, wie z.B. Triethylamin NaOH oder Natriumethylat, zu einem 5-Acyl-3-aryl-2-dialkylaminothiophen des Typs IIIoptionally in the presence of a base, e.g. Triethylamine NaOH or sodium ethylate to a 5-acyl-3-aryl-2-dialkylaminothiophene of type III
IlIl
wobei in den allgemeinen Formeln R einen niederen Alkyl- oder substituierten bzw. unsubstituierten Phenyl-, Naphthyl- oderwherein in the general formulas R is a lower alkyl or substituted or unsubstituted phenyl, naphthyl or
1 Heteroarylrest, R ei&en substituierten oder unsubstituierten Phenyl-, Naphthyl- oder Heteroarylrest, R und R^ gleiche ode verschiedene Alkylreste oder R Ή/ eine Tetramethylen-, Pentamethylen- oder 5-0xapentamethylenbrücke und Hai ein Halogenatom darstellen, umgesetzt wird.1 heteroaryl, R ei & en substituted or unsubstituted phenyl, naphthyl or heteroaryl, R and R ^ are the same ode different alkyl groups or R Ή / a tetramethylene, pentamethylene or 5-oxapentamethylenbrücke and Hal represents a halogen atom is reacted.
Ausführungsbeispieleembodiments
Die nach den verschiedenen Varianten hergestellten 5-Acyl-3~ aryl-2-dialkylaminothiophene vom Typ III sind in Tabelle Λ zusammengestellt.The 5-acyl-3-aryl-2-dialkylaminothiophenes of the type III prepared according to the various variants are compiled in Table Λ .
Variante Aoption A
0,01 Mol substituiertes 3-Hydroxythioacrylamid des Typs I und 0,01 Mol Halogenmethylenverbindung vom Typ II werden in 12 ml Ethanol suspendiert. Man erhitzt die Mischung zum Sied« und gibt 2 ml Triethylamin zu. Nach dem Abkühlen wird das Endprodukt vom Typ III abfiltriert und umkristallisiert.0.01 mole of substituted 3-hydroxythioacrylamide of type I and 0.01 mole of halomethylene compound of type II are suspended in 12 ml of ethanol. The mixture is heated to boiling point and 2 ml of triethylamine are added. After cooling, the end product of type III is filtered off and recrystallized.
Variante BVariant B
Analog Variante A, jedoch werden anstelle des Triethylamin eine Lösung von 0,4 g NaOH in 3 ml Ethanol verwendet.Analog variant A, but instead of the triethylamine, a solution of 0.4 g of NaOH in 3 ml of ethanol are used.
235617 3235617 3
Variante GVariant G
Analog Variante A, jedoch wird das Triethylamin vor dem "Erhitzen der Reaktionsmischung zugegeben.Analog variant A, but the triethylamine is added before the "heating of the reaction mixture.
Variante DVariant D
Analog Variante A, jedoch werden 10 ml Acetonitril anstelle des Ethanols verwendet. ' .' Analog variant A, but 10 ml of acetonitrile are used instead of the ethanol. '.'
2 356 17 32 356 17 3
Tabelle 1: Die nach den verschiedenen Varianten hergestellten 5-Acyl-3-aryl-2-dialkylaminothiophene vom Typ IIITable 1: The prepared according to the different variants 5-acyl-3-aryl-2-dialkylaminothiophene type III
R a) R1 R2R5 Schmp./°C Ausb.Aa R a) R 1 R 2 R 5 m.p./O.C
(Umkrist.) % d. Th(Umkrist.) % D. th
Hal = Br Hal = ClHal = Br Hal = Cl
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD23561781A DD201306A1 (en) | 1981-12-10 | 1981-12-10 | PROCESS FOR THE PREPARATION OF 5-ACYL-3-ARYL-2-DIALKYLAMINOTHIOPHENESE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD23561781A DD201306A1 (en) | 1981-12-10 | 1981-12-10 | PROCESS FOR THE PREPARATION OF 5-ACYL-3-ARYL-2-DIALKYLAMINOTHIOPHENESE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD201306A1 true DD201306A1 (en) | 1983-07-13 |
Family
ID=5535316
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD23561781A DD201306A1 (en) | 1981-12-10 | 1981-12-10 | PROCESS FOR THE PREPARATION OF 5-ACYL-3-ARYL-2-DIALKYLAMINOTHIOPHENESE |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD201306A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006049891A1 (en) * | 2004-10-27 | 2006-05-11 | Janssen Pharmaceutica N.V. | Trisubstituted thiophenes as progesterone receptor modulators |
| US20100152241A1 (en) * | 2008-09-22 | 2010-06-17 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8383670B2 (en) | 2008-08-27 | 2013-02-26 | Calcimedica, Inc. | Trisubstituted thiophenes that modulate intracellular calcium |
| US8618307B2 (en) | 2009-09-16 | 2013-12-31 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
-
1981
- 1981-12-10 DD DD23561781A patent/DD201306A1/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006049891A1 (en) * | 2004-10-27 | 2006-05-11 | Janssen Pharmaceutica N.V. | Trisubstituted thiophenes as progesterone receptor modulators |
| JP2008518011A (en) * | 2004-10-27 | 2008-05-29 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Trisubstituted thiophenes as progesterone receptor modulators |
| US7638525B2 (en) | 2004-10-27 | 2009-12-29 | Janssen Pharmaceutica N.V. | Trisubstituted thiophenes as progesterone receptor modulators |
| CN101087783B (en) * | 2004-10-27 | 2010-12-08 | 詹森药业有限公司 | Trisubstituted thiophenes as progesterone receptor modulators |
| US8383670B2 (en) | 2008-08-27 | 2013-02-26 | Calcimedica, Inc. | Trisubstituted thiophenes that modulate intracellular calcium |
| US8394848B2 (en) | 2008-08-27 | 2013-03-12 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US20100152241A1 (en) * | 2008-09-22 | 2010-06-17 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8524763B2 (en) * | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8618307B2 (en) | 2009-09-16 | 2013-12-31 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
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