DE1141281B - Process for the preparation of acylaminocarboxamides - Google Patents

Process for the preparation of acylaminocarboxamides

Info

Publication number
DE1141281B
DE1141281B DEU6310A DEU0006310A DE1141281B DE 1141281 B DE1141281 B DE 1141281B DE U6310 A DEU6310 A DE U6310A DE U0006310 A DEU0006310 A DE U0006310A DE 1141281 B DE1141281 B DE 1141281B
Authority
DE
Germany
Prior art keywords
acylaminocarboxamides
preparation
reaction
ammonia
mmol
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
DEU6310A
Other languages
German (de)
Inventor
Dr Ivar Ugi
Cornelius Steinbrueckner
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
Priority date (The priority date 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 date listed.)
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/en
Application filed by APOTEKARNES KEMISKA FABRIKER, Astra AB filed Critical APOTEKARNES KEMISKA FABRIKER
Priority to DEU6310A priority patent/DE1141281B/en
Priority to DEU6797A priority patent/DE1237128B/en
Priority to AT25860A priority patent/AT240361B/en
Priority to GB1717/60A priority patent/GB942195A/en
Priority to FR816180A priority patent/FR1363104A/en
Priority to US3745A priority patent/US3247200A/en
Priority to BE586853A priority patent/BE586853A/en
Publication of DE1141281B publication Critical patent/DE1141281B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

INTERNAT. KL. C 07 CINTERNAT. KL. C 07 C

U6310IVb/12oU6310IVb / 12o

ANMELDETAG: 29. JUNI 1959REGISTRATION DATE: JUNE 29, 1959

BEKANNTMACHUNG
DER ANMELDUNG
UNDAUSGABE DER
AUSLEGESCHRIFT: 20. DEZEMBER 1962NOTICE
THE REGISTRATION
AND ISSUE OF
EDITORIAL: DECEMBER 20, 1962

Die Erfindung betrifft ein Verfahren zur Herstellung von Acylaminocarbonsäureamiden.The invention relates to a process for the preparation of acylaminocarboxamides.

Gegenstand des Patents 1 103 337 ist die Herstellung von Aminocarbonsäureamiden und deren Abkömmlingen durch Reaktion eines Aldehyds 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, das am Stickstoffatom mindestens ein Wasserstoffatom besitzt. Vorzugsweise kann dabei in Gegenwart einer als Katalysator wirkenden Säure, z. B. Salzsäure, gearbeitet werden.The subject of patent 1 103 337 is the production of aminocarboxamides and their Derivatives by reaction of an aldehyde or a ketone with an amine or the resulting from it Schiff's base or the corresponding enamine with an isonitrile in the presence of water, Azides, acetic acid or an amine which has at least one hydrogen atom on the nitrogen atom. Preferably, in the presence of an acid acting as a catalyst, eg. B. hydrochloric acid worked will.

Es wurde nun gefunden, daß Acylaminocarbonsäureamide auch durch Umsetzung von Aldehyden oder Ketonen und Ammoniak mit Isonitrilen in Gegenwart von Carbonsäuren oder carbonsauren Salzen bequem zugänglich sind.It has now been found that acylaminocarboxamides can also be obtained by reacting aldehydes or ketones and ammonia with isonitriles in the presence of carboxylic acids or carboxylic acids Salts are easily accessible.

Das folgende Reaktionsschema veranschaulicht die Erfindung in einer einfachen Ausführungsform, wobei iso-Butyraldehyd und Ammoniak mit Cyclohexylisocyanid in Gegenwart von Essigsäure in einem geeigneten Lösungsmittel zur Reaktion gebrächt werden:The following reaction scheme illustrates the invention in a simple embodiment, being iso-butyraldehyde and ammonia with cyclohexyl isocyanide in the presence of acetic acid in a suitable solvent for reaction will:

CH3 CH 3

CH3 CH 3

Verfahren zur Herstellung von
AcylaminocarbonsäureamidenProcess for the production of
Acylaminocarboxamides

Zusatz zum Patent 1 103 337Addendum to patent 1 103 337

Anmelder:Applicant:

Aktiebolaget Astra,Aktiebolaget Astra,

Apotekarnes Kemiska Fabriker,Apotekarnes Kemiska Fabriker,

Södertälje (Schweden)Södertälje (Sweden)

Vertreter: Dr. H.-H. Willrath, Patentanwalt,
Wiesbaden, Hildastr. 18Representative: Dr. H.-H. Willrath, patent attorney,
Wiesbaden, Hildastr. 18th

Dr. Ivar Ugi und Cornelius Steinbrückner, München, sind als Erfinder genannt wordenDr. Ivar Ugi and Cornelius Steinbrückner, Munich, have been named as inventors

CH — CHO + NH3 + CH3COOH + CN — C6Hn CH3 CH - CHO + NH 3 + CH 3 COOH + CN - C 6 Hn CH 3

CH3 CH 3

CO — NH — C6HnCO - NH - C 6 Hn

CH-CHCH-CH

NH — CO — CH3 NH - CO - CH 3

Erfindungsgemäß können somit Acylaminocarbonsäureamide auf einfache Weise hergestellt werden. Diese Verbindungen dienen als Zwischenprodukte und Pharmazeutika.According to the invention, acylaminocarboxamides can thus be prepared in a simple manner. These compounds serve as intermediates and pharmaceuticals.

Beispiel
N-Acetylaminoisovaleriansäure-N'-cyclohexylamidexample
N-acetylaminoisovaleric acid-N'-cyclohexylamide

3,85 g (50 mMol) Ammoniumacetat, ein Tropfen konzentrierte wäßrige Ammoniaklösung 1,80 g (25 mMol) iso-Butyraldehyd und 2,72 g (25 mMol) Cyclohexylisocyanid werden in 20 ecm Methanol und 5 ecm Wasser gelöst und 1 Tag bei Raumtemperatur stehengelassen. Dabei scheidet sich ein Teil des Reaktionsproduktes bereits kristallin ab. Nach dem Absaugen der auskristallisierten Anteile (2,45 g, Schmp.: 230 bis 2310C) wird das Reaktionsgemisch auf ein Drittel des ursprünglichen Volumens eingeengt. Hierbei kristallisieren weitere 864 mg des Produkts aus (Schmp.: 224 bis 229°C).3.85 g (50 mmol) of ammonium acetate, one drop of concentrated aqueous ammonia solution, 1.80 g (25 mmol) of isobutyraldehyde and 2.72 g (25 mmol) of cyclohexyl isocyanide are dissolved in 20 ecm of methanol and 5 ecm of water and added for 1 day Let stand room temperature. Part of the reaction product separates out in crystalline form. After aspiration of the crystallized portions (2.45 g, m.p .: 230-231 0 C), the reaction mixture is concentrated to one-third of the original volume. A further 864 mg of the product crystallize out (melting point: 224 to 229 ° C.).

Das Produkt läßt sich durch Umkristallisieren aus Methanol reinigen. Gesamtausbeute: 3,1.1 g (52% der Theorie), Schmp.: 230,5 bis 231,00C.The product can be purified by recrystallization from methanol. Total yield: 3,1.1 g (52% of theory), m.p .: 230.5 to 231.0 0 C.

Claims (1)

Patentanspruch.Claim. Verfahren zur Herstellung von Acylaminocarbonsäureamiden durch Reaktion von Aldehyden oder Ketonen und Aminen mit Isonitrilen in Gegenwart von Carbonsäuren bzw. deren Salzen nach Patent 1 103 337, dadurch gekenn zeichnet, daß man an Stelle der Amine Ammoniak verwendet.Process for the preparation of acylaminocarboxamides by reaction of aldehydes or ketones and amines with isonitriles in the presence of carboxylic acids or their salts according to Patent 1 103 337, characterized in that ammonia is used instead of the amines.
DEU6310A 1959-01-22 1959-06-29 Process for the preparation of acylaminocarboxamides Pending DE1141281B (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
NL247576D NL247576A (en) 1959-01-22
NL132442D NL132442C (en) 1959-01-22
DEU5930A DE1103337B (en) 1959-01-22 1959-01-22 Process for the preparation of aminocarboxamides and their Abkoemmlingen
DEU6310A DE1141281B (en) 1959-06-29 1959-06-29 Process for the preparation of acylaminocarboxamides
DEU6797A DE1237128B (en) 1959-01-22 1960-01-08 Process for the preparation of aminocarboxamides, which atom group contain
AT25860A AT240361B (en) 1959-01-22 1960-01-14 Process for the preparation of substituted aminocarboxamides
GB1717/60A GB942195A (en) 1959-01-22 1960-01-18 Method of preparing compounds containing the group
FR816180A FR1363104A (en) 1959-01-22 1960-01-20 Process for the manufacture of compounds containing the nccn group, compounds thus obtained and their applications
US3745A US3247200A (en) 1959-01-22 1960-01-21 Process for preparing amino-carboxylic acid amides
BE586853A BE586853A (en) 1959-01-22 1960-01-22 Process for the manufacture of compounds containing the NCCN group, compounds thus obtained and their applications.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEU6310A DE1141281B (en) 1959-06-29 1959-06-29 Process for the preparation of acylaminocarboxamides

Publications (1)

Publication Number Publication Date
DE1141281B true DE1141281B (en) 1962-12-20

Family

ID=7565748

Family Applications (1)

Application Number Title Priority Date Filing Date
DEU6310A Pending DE1141281B (en) 1959-01-22 1959-06-29 Process for the preparation of acylaminocarboxamides

Country Status (1)

Country Link
DE (1) DE1141281B (en)

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