DD154363A1 - METHOD FOR PRODUCING THIOPHENIC CARBOXYLIC ACID BENZYL AMIDES - Google Patents
METHOD FOR PRODUCING THIOPHENIC CARBOXYLIC ACID BENZYL AMIDES Download PDFInfo
- Publication number
- DD154363A1 DD154363A1 DD21281379A DD21281379A DD154363A1 DD 154363 A1 DD154363 A1 DD 154363A1 DD 21281379 A DD21281379 A DD 21281379A DD 21281379 A DD21281379 A DD 21281379A DD 154363 A1 DD154363 A1 DD 154363A1
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- DD
- German Democratic Republic
- Prior art keywords
- carboxylic acid
- benzylamides
- preparation
- general formula
- thiophenic
- Prior art date
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- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Ziel der Erfindung ist es, ein Verfahren fuer die Herstellung von 5-Amino-2-aryl-, arylmethyl- bzw. hetarylmethylamino-5-nitro-thiophen-3-carbonsaeure-bezylamiden zu entwickeln. Die Thiophencarbonsaeure-benzylamide der allgemeinen Formel II, in der R fuer einen gegebenenfalls alkyl-, alkoxy - oder halogensubstituierten Phenyl-, Benzyl - bzw. Hetarylmethylrest steht, koennen durch Umsetzung der Cyanessigsaeure-benzylamide der allgemeinen Formel I, in der R wie oben definiert ist, mit Bromnitromethan in Gegenwart von Alkalien hergestellt werden. Diese Thiophencarbonsaeure-benzylamide koennen als organische Zwischenprodukte fuer weitere Synthesen verwendet werden. Sie sind insbesondere zur Herstellung kondensierter Heterocyclen geeignet.The aim of the invention is to develop a process for the preparation of 5-amino-2-aryl, arylmethyl or hetarylmethylamino-5-nitro-thiophene-3-carboxylic acid bezylamiden. The thiophenecarboxylic acid benzylamides of the general formula II in which R is an optionally alkyl-, alkoxy- or halogen-substituted phenyl, benzyl or hetarylmethyl radical can be prepared by reacting the cyanoacetic acid benzylamides of the general formula I in which R is as defined above is to be prepared with bromonitromethane in the presence of alkalis. These thiophenecarboxylic acid benzylamides can be used as organic intermediates for further syntheses. They are particularly suitable for the preparation of condensed heterocycles.
Description
212813212813
Verfahren zur Herstellung von ThiophencarbonsäurebenzylamidenProcess for the preparation of thiophenecarboxylic acid benzylamides
Die Erfindung betrifft ein Verfahren zur Herstellung von ^Amlno-Z-aryl-, arylmethyl- bzw. hetarylmethylamino-5-nitro-thiophen-3-carbonsäure-benzylamiden. Liese Thlophencarbonsäure-benzylamlde können als organische Zwischenprodukte für weitere Synthesen verwendet werden. Sie sind insbesondere zur Herstellung kondensierter Heterocyclen geeignet.The invention relates to a process for the preparation of ^ amno-Z-aryl, arylmethyl or hetarylmethylamino-5-nitro-thiophene-3-carboxylic acid benzylamides. Liese thlophenecarboxylic acid benzylamides can be used as organic intermediates for further syntheses. They are particularly suitable for the preparation of condensed heterocycles.
4—Aralno-2-aryl-, arylmethyl- bzw. hetarylmethylamino-5-nitro-thiophen-3-carbonsäure~benzylamlde sind bisher noch nicht bekannt·4-Aralno-2-aryl, arylmethyl or hetarylmethylamino-5-nitro-thiophene-3-carboxylic acid benzylamides are not yet known
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist es, ein Verfahren für die Herstellung dieser Thiophencarbonsäure-benzylamide zu entwickeln.The aim of the invention is to develop a process for the preparation of these thiophenecarboxylic acid benzylamides.
Die Thiophencarbonsaure-benzylamide der allgemeinen Formel II* in der R für einen gegebenenfalls alkyl-, alkoxy- oder halogensubstituierten Phenyl-, Benzyl- bzw, Hetarylmethylrest stehtj können durch Umsetzung der Cyanessigsäure-benzylaraide der allgemeinen Formel I, in der R wie oben definiert ist, mit Bromnitromethan in Gegenwart von AlkalienThe thiophenecarboxylic acid benzylamides of the general formula II * in which R is an optionally alkyl-, alkoxy- or halogen-substituted phenyl, benzyl or hetarylmethyl radical can be prepared by reacting the cyanoacetic acid benzylareas of the general formula I in which R is as defined above , with bromonitromethane in the presence of alkalis
- 2 - O 1 O Q * O j j- 2 - O 1 O Q * O j j
212813212813
hergestellt werden. jgetting produced. j
Die Umsetzungen werden in organischen Lösungsmitteln,vor- i zugsweise in Alkoholen, in Gegenwart von Alkalien, vor- j zugsweise Alkoholaten, durchgeführt. Die Reaktionstempe- j raturen liegen zwischen 10° und 5O0C. Die Reaktionszeit ; beträgt 5 Minuten bis zu 2 Stunden· Die Reaktionsprodukte fallen entweder aus der Reaktionsmischung aus bzw. werden nach dem Einengen im Vakuum oder durch Fällen mit Wasser kristallin erhalten. Sie können durch Ümkristallisieren aus organischen Lösungsmitteln weiter gereinigt werden.The reactions are carried out in organic solvents, preferably in alcohols, in the presence of alkalis, preferably alcoholates. The temperatures Reaktionstempe- j are between 10 ° and 5O 0 C. The reaction time; is 5 minutes to 2 hours · The reaction products either precipitate from the reaction mixture or are obtained after concentration in vacuo or by precipitation with water crystalline. They can be further purified by recrystallization from organic solvents.
4-Amino-2-(fur-2-yl-met hylaminoJ-5-nitro-thiophen-3-carbonsäure-benzylamid4-Amino-2- (fur-2-yl-metylamino) J-5-nitro-thiophene-3-carboxylic acid benzylamide
Man lost nacheinander 0,01 Mol Natrium und 0,01 Mol 3-[Fur^-yl-methylaminoj^-mercapto^-cyano-acrylsäurebenzylamid in 20 ml absolutem Ethanol· Tropfenweise werden dann unter Rühren 0,01 Mol Bromnitromethan hinzugefügt. Man rührt dann noch 15 Minuten weiter, versetzt mit 50 ml Wasser, filtriert ab, wäscht den Niederschlag mit V/asser und kristallisiert diesen aus Eisessig um. Ausbeute: 42$ d.Th. Schmelzpunkt: 212-2140C0.01 mol of sodium and 0.01 mol of 3- [fur ^ -yl-methylamino] -mercapto-cyanoacrylic acid benzylamide in 20 ml of absolute ethanol are dissolved in succession. Dropwise, 0.01 mol of bromonitromethane are then added with stirring. The mixture is then stirred for a further 15 minutes, mixed with 50 ml of water, filtered off, washed with precipitate with water and crystallized from glacial acetic acid. Yield: 42 $ d.Th. Melting point: 212-214 0 C
(Zersetzung)(Decomposition)
2128 13 -1- 2128 13 -1-
C6H5CH2NHCO ^NHRC 6 H 5 CH 2 NHCO 4 NHR
NC SHNC SH
+ BrCH2NO2 + BrCH 2 NO 2
C6H5CH2NHCO-CC 6 H 5 CH 2 NHCO-C
C-MRC-MR
NO IINO II
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD21281379A DD154363A1 (en) | 1979-05-11 | 1979-05-11 | METHOD FOR PRODUCING THIOPHENIC CARBOXYLIC ACID BENZYL AMIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD21281379A DD154363A1 (en) | 1979-05-11 | 1979-05-11 | METHOD FOR PRODUCING THIOPHENIC CARBOXYLIC ACID BENZYL AMIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD154363A1 true DD154363A1 (en) | 1982-03-17 |
Family
ID=5518087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD21281379A DD154363A1 (en) | 1979-05-11 | 1979-05-11 | METHOD FOR PRODUCING THIOPHENIC CARBOXYLIC ACID BENZYL AMIDES |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD154363A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040034A1 (en) * | 1996-04-22 | 1997-10-30 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted thiophenes and of arrays of substituted thiophenes |
-
1979
- 1979-05-11 DD DD21281379A patent/DD154363A1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997040034A1 (en) * | 1996-04-22 | 1997-10-30 | Novo Nordisk A/S | Solid phase and combinatorial synthesis of substituted thiophenes and of arrays of substituted thiophenes |
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