DE1237128B - Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten - Google Patents

Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten

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Publication number
DE1237128B
DE1237128B DEU6797A DEU0006797A DE1237128B DE 1237128 B DE1237128 B DE 1237128B DE U6797 A DEU6797 A DE U6797A DE U0006797 A DEU0006797 A DE U0006797A DE 1237128 B DE1237128 B DE 1237128B
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DE
Germany
Prior art keywords
acid
aminocarboxamides
ecm
preparation
ketone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
DEU6797A
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English (en)
Inventor
Dr Ivar Ugi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
APOTEKARNES KEMISKA FABRIKER
AstraZeneca AB
Original Assignee
APOTEKARNES KEMISKA FABRIKER
Astra AB
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Filing date
Publication date
Priority to NL247576D priority Critical patent/NL247576A/xx
Priority to NL132442D priority patent/NL132442C/xx
Priority to DEU5930A priority patent/DE1103337B/de
Priority claimed from DEU6310A external-priority patent/DE1141281B/de
Application filed by APOTEKARNES KEMISKA FABRIKER, Astra AB filed Critical APOTEKARNES KEMISKA FABRIKER
Priority to DEU6797A priority patent/DE1237128B/de
Priority to AT997663A priority patent/AT240374B/de
Priority to AT997763A priority patent/AT240358B/de
Priority to AT25860A priority patent/AT240361B/de
Priority to GB1717/60A priority patent/GB942195A/en
Priority to FR816180A priority patent/FR1363104A/fr
Priority to US3745A priority patent/US3247200A/en
Priority to BE586853A priority patent/BE586853A/fr
Publication of DE1237128B publication Critical patent/DE1237128B/de
Pending legal-status Critical Current

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    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
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    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
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    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
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    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
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    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
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    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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  • General Health & Medical Sciences (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

SUNDESKEPUBLIK DEUTSCHLAND Int. CL:
C 07 c
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Deutsche Kl.: 12 q-6/01
Nummer: 1237 128
Aktenzeichen: U 6797 IV b/12 q
Anmeldetag: 8. Januar 1960
Auslegetag: 23. März 1967
Die Erfindung betrifft ein Verfahren zur Herstellung von Aminocarbonsäureamiden, welche die Atomgruppierung
N—C—C—N
enthalten.
Gegenstand des Hauptpatentes 1 103 337 ist die Herstellung von Aminocarbonsäureamiden und deren Abkömmlingen durch Reaktion eines Aldehydes oder eines Ketons mit einem Amin bzw. der hieraus entstehenden Schiffschen Base oder dem entsprechenden Enamin mit einem Isonitril in Gegenwart von Wasser, Aziden, Essigsäure oder einem Amin. Vorzugsweise kann dabei in Gegenwart einer als Katalysator wirkenden Säure, z. B. Salzsäure, gearbeitet werden.
Es wurde nun gefunden, daß sich Aminocarbonsäureamide besonderer Art auch durch die Umsetzung von Aldehyden oder Ketonen und Ammoniak mit Isonitrilen in Gegenwart anderer Säureionen herstellen lassen, indem man erfindungsgemäß als Säureanionen Selenid-, Nitrat- oder ein aliphatisches Polycarbonsäureanion oder eine Lösung von Kohlendioxyd in Methanol verwendet.
Die für das Verfahren nach der Erfindung notwendigen Isonitrile sind in jüngster Zeit leicht zugänglich geworden (s. I. U g i und R. M e y r, Angew. Chem., 70 [1958], S. 702). Für das Verfahren nach der Erfindung kommen aliphatische, aromatische, araliphatische oder heterozyklische Isonitrile in Betracht. Beispiele geeigneter Isonitrile sind Isopropyl-isocyanid, n-Butyl-isocyanid, tert.-Butyl-isocyanid, Cyclohexylisoeyanid, Benzyl-isocyanid, Pyridyl-isocyanid und 2,6-Dimethylphenyl-isocyanid.
Das für die Reaktion erforderliche Imoniumion kann auf verschiedene Weise bereitgestellt werden. Es können Verbindungen eingesetzt werden, in denen das Imoniumion bereits vorliegt, beispielsweise ViIsmeier-Addukte (vgl. zum Beispiel C. Jutz, Chem. Ben, 91 [1958], S. 850) oder Hydrastininchlorid. Eine andere Quelle für das Imoniumion stellt die Addition eines Protons an Schiffsche Basen oder Enamine dar. Schiffsche Basen und Enamine sind Kondensationsprodukte von Aminen mit Ketonen oder Aldehyden, ebenso wie Dien-amine und N-Acetale, welche ebenfalls durch Säureeinwirkung Imoniumionen zu bilden vermögen. Derartige Kondensationsprodukte von Carbonylverbindungen und Aminen brauchen nicht unbedingt vorgebildet vorzuliegen, sondern sie können vielfach auch zweckmäßig während der Reaktion erst selbst gebildet werden, indem man die Ausgangs-Verfahren zur Herstellung
von Aminocarbonsäureamiden, welche die
Atomgruppierung N-C-C-N enthalten
Zusatz zum Patent: 1103 337
Anmelder:
Aktiebolaget Astra,
Apotekarnes Kemiska Fabriker,
Södertälje (Schweden)
Vertreter:
Dr. H.-H. Willrath, Patentanwalt,
Wiesbaden, Hildastr. 18
Als Erfinder benannt:
Dr. Ivar Ugi,
Cornelius Steinbrückner, München
materialien für diese Kondensationsprodukte, wie Aldehyde und Amine, direkt in die Reaktion einsetzt.
Als Aldehyd oder Keton kommen beispielsweise in
Frage: Formaldehyd, Acetaldehyd, Propionaldehyd, n-Butyraldehyd, Isobutyraldehyd, Benzaldehyd, Ferrocenaldehyd, Pyridinaldehyd, Benzothiazolaldehyd, Succindialdehyd, l-Azulen-l'-propen-l-al, Propinal und die daraus durch Addition von Aminen erhaltenen ß-Aminoacroleine, ferner Dimethylaminozimtaldehyd, (β-Methylmercapto-propionaldehyd, Trifluorbutyraldehyd, ß-Dimethylaminopivalinaldehyd, Methyläthylketon, Aceton, Diäthylketon, Methylpropylketon, Äthylpropylketon, Dipropylketon, Dibutylketon, Benzylmethylketon, Dibenzylketon und Cyclohexanon.
Als Aminkomponenten der Imoniumionen können eingesetzt werden: Ammoniak oder primäre oder sekundäre Mono- oder Diamine sowie deren Salze wie Methylamin, Dimethylamin, Äthylamin, Diäthylamin, Diäthanolamin, Propylamin, Dipropylamin, y-Chlorpropylamin, Butylamin, Methyloctylamin, Dibutylamin, Octamethylendiamin, N,N'-Dimethylhexamethylendiamin, Trimethyläthylendiamin, Piperidin, Morpholin, Cyclohexylamin, Benzylamin, substituierte Benzylamine, z. B. 3,4-Dichlorbenzylamin,
709 520/413
Phenyläthylamin, Anilin, substituierte Aniline, Hydrazin und dessen Alkyl-, Aryl- und Acylderivate, Hydroxylamin und dessen Monoalkyl- und Monoarylderivate.
Allgemein verläuft die Reaktion nach der Erfindung wie folgt:
©
^N--C < + :C = N —R + B3 / Imoniumion Isonitril Nucleophiler
Partner
\ I I
^f > ^N-C-C=N-R
' Primäraddukt
Das Primäraddukt stabilisiert sich in einer durch seine Konstitution gegebenen Sekundärreaktion zum isolierbaren Endprodukt. Welcher Art die Sekundärreaktion sein kann, mögen die nachstehenden Beispiele erläutern:
Spielt z. B. Selenwasserstoff die Rolle des nucleophilen Partners, so führt bereits eine Protonenverschiebung zu einem stabilen Endprodukt
SeH
:n—c—c;
R'
Se
:n — c — c — n;
Andere Sekundärreaktionen laufen auch ab im Falle von Kohlensäurederivaten. Sind in den vorstehend besprochenen gemischten Anhydriden keine acylierbaren Gruppen vorhanden, weil z. B. von sekundärem Amin ausgegangen wurde, so erfolgt die Stabilisierung des reaktiven Systems dadurch, daß die Acylgruppe in anderer Weise intermolekular übertragen wird.
Bei Durchführung der Reaktion setzt man die ίο notwendigen Komponenten in beliebiger Reihenfolge zu. Vorzugsweise führt man die Reaktion in geeigneten Lösungsmitteln aus, wie z. B. in Methanol, Benzol, Tetrahydrofuran, Aceton, Chloroform oder Wasser. Die Reaktion erfolgt ganz glatt bei Mischung der Ausgangsmaterialien bei Zimmertemperatur, und es ist in gewissen Fällen erforderlich, Eiskühlung anzuwenden, um die Reaktion zu mäßigen.
Die Erfindung wird durch folgende Beispiele erläutert:
Beispiel 1
Λ-Piperidino-selenoisovaleriansäure-cyclohexylamid
Zu 5,0 g Natriumselenid und 3,0 ecm Cyclohexylisocyanid wird unter Rühren eine Lösung von 3,4 g Piperidin, 3,2 ecm konzentrierte Salzsäure und 2,16 g Isobutyraldehyd in 40 ecm Methanol und 20 ecm Wasser zugetropft. Nach 20stündigem Rühren wird von einem geringen Niederschlag abfiltriert und die Lösung eingeengt. Der Rückstand wird mit Petroläther ausgezogen. Der Extrakt wird eingeengt. Es werden 3,2 g farblose Kristalle vom Schmelzpunkt 154 bis 157° C (Zersetzung) erhalten.
Beispiel 2
N", N*'-Adipinyl-bis-(a-methylamino-isovaleriansäure-isopropylamid)
CH3 — N — CO — (CH2)4 — CO N — CH.
CH — CO — NH — CH(CHg)2 CH — CONH — CH(CH3).,
CH(CH3)* CH — (CH3)2
5 g einer wäßrigen 35°/oigen Methylaminlösung, 4,32 g Isobutyraldehyd und 4,38 g Adipinsäure werden in 5 ecm Wasser und 40 ecm Methanol eingetragen. Unter Rühren und Eiskühlung werden 1,72 g Isopropyl-isocyanid zugetropft. Nach 2wöchigem Stehen bei Raumtemperatur unter gelegentlichem Umschütteln wird das Lösungsmittel abgezogen. Das entstandene Säureamid wird aus Methanol umkristallisiert. Die Ausbeute beträgt 5,8 g an hochschmelzendem Produkt.
Beispiel 3
N-n-Butyl-N-carbomethoxy-a-amino-isovaleriansäure-N'-cyclohexylamid
3,65 g N-Butylamin werden in 50 ecm Methanol gelöst. Die Lösung wird bis zur Sättigung mit festem Kohlendioxyd als Reaktionspartner versetzt. Als Zwischenprodukt bildet sich Kohlensäuremonomethylester. Nun werden 3,0 ecm Cyclohexylisocyanid und 2,84 g Isobutyraldehyd zugegeben. Nach 20 Stunden Stehen wird die Lösung im Vakuum eingeengt. Es werden 7,6 g Rohprodukt erhalten. Durch Umkristallisation aus Petroläther werden 4,2 g farblose Kristalle vom Schmelzpunkt 66 bis 680C erhalten.
Beispiel 4
N-n-Butyl-N-nitro-Ä-amino-isovaleriansäure-N'-cyclohexylamid
2,19 g n-Butylamin, 2,44 ecm konzentrierte Salzsäure, 2,73 ecm Isobutyraldehyd, 11,8 g Calciumnitrat, 5 ecm Wasser und 25 ecm Methanol werden zusammengegeben und bei Raumtemperatur 30 Stunden stehengelassen. Das Lösungsmittel wird im Vakuum abgezogen und der Rückstand mit Benzol aufgenommen. Die benzolische Lösung wird mit 2n-Salzsäure ausgeschüttelt, getrocknet und eingeengt. Es bleiben 3,3 g eines farblosen Öles zurück, das entsprechend seinem IR-Spektrum sowohl ein Nitraminderivat als auch ein Carbonsäureamid ist.

Claims (1)

  1. 5 6
    Patentanspruch: eines Ketons und eines Amins bzw. der daraus
    Verfahren zur Herstellung von Aminocarbon- entstehenden Schiffschen Base oder des ent-
    säureamiden, welche die Atomgruppierung sprechenden Enamins mit einem Isonitnl in
    Gegenwart von Saureamonen nach Patent I I 5 1103 337, dadurch gekennzeichnet,
    N-C C N daß man als Säureanion ein Selenid-, Nitrat-
    I I oder ein aliphatisches Polycarbonsäureanion oder
    eine Lösung von Kohlendioxyd in Methanol enthalten, durch Umsetzung eines Aldehyds oder verwendet.
    709 520/413 3.67 © Bundesdruckerei Berlin
DEU6797A 1959-01-22 1960-01-08 Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten Pending DE1237128B (de)

Priority Applications (11)

Application Number Priority Date Filing Date Title
NL247576D NL247576A (de) 1959-01-22
NL132442D NL132442C (de) 1959-01-22
DEU5930A DE1103337B (de) 1959-01-22 1959-01-22 Verfahren zur Herstellung von Aminocarbonsaeureamiden und deren Abkoemmlingen
DEU6797A DE1237128B (de) 1959-01-22 1960-01-08 Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten
AT25860A AT240361B (de) 1959-01-22 1960-01-14 Verfahren zur Herstellung von substituierten Aminocarbonsäureamiden
AT997663A AT240374B (de) 1960-01-08 1960-01-14 Verfahren zur Herstellung von β-Lactamen
AT997763A AT240358B (de) 1959-01-22 1960-01-14 Verfahren zur Herstellung von 1, 5-disubstituierten Tetrazolen
GB1717/60A GB942195A (en) 1959-01-22 1960-01-18 Method of preparing compounds containing the group
FR816180A FR1363104A (fr) 1959-01-22 1960-01-20 Procédé de fabrication de composés contenant le groupement nccn, composés ainsi obtenus et leurs applications
US3745A US3247200A (en) 1959-01-22 1960-01-21 Process for preparing amino-carboxylic acid amides
BE586853A BE586853A (fr) 1959-01-22 1960-01-22 Procédé de fabrication de composés cóntenant le groupement NCCN, composés ainsi obtenus et leurs applications.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEU5930A DE1103337B (de) 1959-01-22 1959-01-22 Verfahren zur Herstellung von Aminocarbonsaeureamiden und deren Abkoemmlingen
DEU6310A DE1141281B (de) 1959-06-29 1959-06-29 Verfahren zur Herstellung von Acylaminocarbonsaeureamiden
DEU6797A DE1237128B (de) 1959-01-22 1960-01-08 Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten

Publications (1)

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DE1237128B true DE1237128B (de) 1967-03-23

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DEU5930A Pending DE1103337B (de) 1959-01-22 1959-01-22 Verfahren zur Herstellung von Aminocarbonsaeureamiden und deren Abkoemmlingen
DEU6797A Pending DE1237128B (de) 1959-01-22 1960-01-08 Verfahren zur Herstellung von Aminocarbonsaeureamiden, welche die Atomgruppierung ? enthalten

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US (1) US3247200A (de)
AT (1) AT240361B (de)
BE (1) BE586853A (de)
DE (2) DE1103337B (de)
GB (1) GB942195A (de)
NL (2) NL132442C (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3549340A (en) * 1967-12-19 1970-12-22 Lubrizol Corp Fuel compositions and additives
US3975443A (en) * 1972-06-06 1976-08-17 Allen & Hanburys Limited 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine
US3979380A (en) * 1972-10-27 1976-09-07 American Home Products Corporation Derivatives of imidazolidin-2-ones and -2-thiones
US4601839A (en) * 1978-06-19 1986-07-22 The B. F. Goodrich Company Stabilized polymers, novel stabilizers, and synthesis thereof
US4310429A (en) * 1978-06-19 1982-01-12 The B. F. Goodrich Company Stabilized polymers, novel stabilizers, and synthesis thereof
US4762872A (en) * 1985-11-01 1988-08-09 The B. F. Goodrich Company Oligomeric light stabilizers with substituted piperidine ends
EP0910565A1 (de) * 1997-02-14 1999-04-28 Bayer Corporation Amidderivate als selektive neuropeptid-y-rezeptoren
US6048900A (en) * 1998-02-13 2000-04-11 Bayer Corporation Amide derivatives and methods for using the same as selective neuropeptide Y receptor antagonists
CN116333313A (zh) * 2023-03-15 2023-06-27 华南理工大学 一种聚酰胺基硫脲类化合物及其制备方法与应用

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Publication number Priority date Publication date Assignee Title
US2602794A (en) * 1952-07-08 Process for preparation of x-amino-s
US2235638A (en) * 1936-10-09 1941-03-18 Merck & Co Inc Process of preparing derivatives of pyrimidine

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Publication number Publication date
NL247576A (de)
US3247200A (en) 1966-04-19
AT240361B (de) 1965-05-25
DE1103337B (de) 1961-03-30
BE586853A (fr) 1960-07-22
GB942195A (en) 1963-11-20
NL132442C (de)

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