DE1160444B - Process for the preparation of aminocarboxylic acid amides - Google Patents
Process for the preparation of aminocarboxylic acid amidesInfo
- Publication number
- DE1160444B DE1160444B DEU8724A DEU0008724A DE1160444B DE 1160444 B DE1160444 B DE 1160444B DE U8724 A DEU8724 A DE U8724A DE U0008724 A DEU0008724 A DE U0008724A DE 1160444 B DE1160444 B DE 1160444B
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- acid amides
- aminocarboxylic acid
- aminocarboxamides
- production
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Aminocarbonsäureamiden Zusatz zum Patent: 1103 337 Gegenstand des Patents 1103 337 ist ein Verfahren zur Herstellung von Aminocarbonsäureamiden und deren Abkömmlingen, das dadurch gekennzeichnet ist, daß man einen Aldehyd oder ein Keton mit einem Amin bzw. die hieraus entstehende Schiffsche Base oder das entsprechende Enamin mit einem Isonitril in Gegenwart von Wasser oder Aziden, Essigsäure oder einem Amin umsetzt, das am Stickstoffatom mindestens ein Wasserstoffatom besitzt.Process for the production of aminocarboxamides Addition to the patent: 1103 337 The subject of patent 1103 337 is a process for the preparation of aminocarboxamides and their derivatives, which is characterized in that one aldehyde or a ketone with an amine or the resulting Schiff base or the corresponding one Enamine with an isonitrile in the presence of water or azides, acetic acid or converts an amine which has at least one hydrogen atom on the nitrogen atom.
Es wurde nun in Weiterausbildung des Verfahrens zur Herstellung von Aminocarbonsäureamiden durch Umsetzung von Aldehyden oder Ketonen mit Aminoverbindungen und Isonitrilen gemäß Patent 1103 337 gefunden, daß man Lactam-N-carbonsäureamide erhält, wenn man an Stelle von Aminen in Gegenwart von Essigsäure Aminocarbonsäuren verwendet. It has now been trained in the process of making Aminocarboxamides by reacting aldehydes or ketones with amino compounds and isonitriles according to patent 1103 337 found that lactam-N-carboxamides obtained when, instead of amines, aminocarboxylic acids are obtained in the presence of acetic acid used.
Das folgende Reaktionsschema veranschaulicht z. B. die Umsetzung von iso-Butyraldehyd und B-Alanin mit Cyclohexylisocyanid: Es können somit Lactame der Aminocarbonsäureamide, insbesondere P-Lactame, auf einfache Weise hergestellt werden. Diese Verbindungen dienen als Zwischenprodukte und Pharmazeutika.The following reaction scheme illustrates e.g. B. the reaction of isobutyraldehyde and B-alanine with cyclohexyl isocyanide: Lactams of the aminocarboxamides, in particular P-lactams, can thus be produced in a simple manner. These compounds serve as intermediates and pharmaceuticals.
Beispiel ß-Propiolactam-N-a-isovaleriansäure-N'-cyclohexylamid 2,6 g (30 mMol) ß-Alanin in 80 ccm Methanol werden mit zwei Plätzchen Kaliumhydroxyd, 2,16 g (30 mMol) iso-Butyraldehyd und 2,72 g (25 mMol) Cyclohexylisonitril versetzt und 24 Stunden bei Raumtemperatur gerührt. Das Methanol wird im Wasserstrahlvakuum bei einer Badtemperatur von annähernd 400 C abgezogen. Der ölige Rückstand wird nach einem Tag wachsartig fest. Rohausbeute: 4,41 g (700/0 der Theorie); Schmp.: 79 bis 92°C. Example β-propiolactam-N-α-isovaleric acid-N'-cyclohexylamide 2,6 g (30 mmol) of ß-alanine in 80 ccm of methanol are mixed with two cookies of potassium hydroxide, 2.16 g (30 mmol) of isobutyraldehyde and 2.72 g (25 mmol) of cyclohexylisonitrile were added and stirred for 24 hours at room temperature. The methanol is in a water jet vacuum withdrawn at a bath temperature of approximately 400 C. The oily residue will waxy solid after one day. Crude yield: 4.41 g (700/0 of theory); M.p .: 79 to 92 ° C.
Das Rohprodukt wird in Methanol aufgenommen, vom Unlöslichen abfiltriert und zweimal mit je 10 ccm einer 50/oigen primären Natriumphosphatlösung ausgeschüttelt und mit Kaliumcarbonat getrocknet. Das Lösungsmittel wird im Vakuum abgezogen. Das gereinigte ß-Propiolactam-N-a-isovaleriansäure-N'-cyclohexylamid hat einen Schmp. von 95 bis 97"C.The crude product is taken up in methanol and the insolubles are filtered off and shaken out twice with 10 cc each of a 50% primary sodium phosphate solution and dried with potassium carbonate. The solvent is removed in vacuo. That Purified ß-propiolactam-N-a-isovaleric acid-N'-cyclohexylamide has a melting point. from 95 to 97 "C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU8724A DE1160444B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of aminocarboxylic acid amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU8724A DE1160444B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of aminocarboxylic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1160444B true DE1160444B (en) | 1964-01-02 |
Family
ID=7566505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU8724A Pending DE1160444B (en) | 1959-06-29 | 1959-06-29 | Process for the preparation of aminocarboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1160444B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322345A (en) | 1977-09-30 | 1982-03-30 | Kyowa Hakko Kogyo Kabushiki Kaisha | 2-Azetidinone 4-carboxy derivatives and a process for producing the same |
-
1959
- 1959-06-29 DE DEU8724A patent/DE1160444B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4322345A (en) | 1977-09-30 | 1982-03-30 | Kyowa Hakko Kogyo Kabushiki Kaisha | 2-Azetidinone 4-carboxy derivatives and a process for producing the same |
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