CH315083A - Process for the preparation of a new aldehyde derivative - Google Patents
Process for the preparation of a new aldehyde derivativeInfo
- Publication number
- CH315083A CH315083A CH315083DA CH315083A CH 315083 A CH315083 A CH 315083A CH 315083D A CH315083D A CH 315083DA CH 315083 A CH315083 A CH 315083A
- Authority
- CH
- Switzerland
- Prior art keywords
- aldehyde derivative
- pyridine
- amide
- dicarboxylic acid
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Aldehydderivates Gegenstand des Patentes ist ein Verfah ren zur Herstellung eines neuen Aldehyd derivates, welches gute keimtötende Eigen schaften besitzt. Die Verbindung und haupt sächlich auch ihre löslichen Salze sollen zur Bekämpfung von Infektionskrankheiten ver wendet werden.
Das den Gegenstand des Patentes bildende Verfahren ist dadurch gekennzeichnet, dass man auf Pyridin-2,5-dicarbonsäure-5-amid Formaldehyd einwirken, lässt, wobei sich das Pyridin-2,5-dicarbonsättre-5-N-oxymethyl-amid bildet. Der Formaldehyd kann beispielsweise auch einer Formaldehyd liefernden Verbin dung, z. B. einem polymeren Formaldehyd (Triozymethylen, Paraformaldehyd), entstam men. Vorzugsweise wird die Umsetzung in alkalischem Milieu vorgenommen, da beim Arbeiten unter pH-7 leicht unerwünschte Ne benprodukte entstehen.
<I>Beispiel</I> 200 g Pyridin-2,5-dicarbonsäure-5-amid werden in 600 cm3 Wasser aufgeschlämmt und unter Rühren verdünnte Natronlauge 1 :10 bis p$ = 9 zugesetzt. Man erwärmt auf dem Wasserbad auf 80 und verrührt mit 450 cm3 361/oiger wässeriger Formaldehydlösung. Man hält 15 Minuten bei 80 und stellt die Was serstoffionenkonzentration mit Hilfe von Na tronlauge auf einen Wert von 9-10 ein. Da nach setzt man Aktivkohle zu, filtriert und neutralisiert mit Ameisensäure genau auf p$ 7. Anschliessend rührt man Aceton ein, bis ein Niederschlag entsteht.
Derselbe wird nach 24 Stunden abgesaugt und mit Aceton gewaschen. Durch Vakuumtrocknung bei 30 bis 40 erhält man das Natriumsalz des Pyridin- 2,5-dicarbonsäure-5-N-oxymethyl-amids als farbloses Pulver, das sich in kaltem Wasser bis zu 20 /o mit praktisch neutraler Reaktion löst.
Das so erhaltene Natriumsalz kann sehr leicht aus Wasser mit Hilfe von Aceton um gefällt werden.
Die freie Verbindung kann durch vor sichtiges Ansäuern der wässerigen Lösung eines Salzes des Pyridin-2,5-dicarbonsäure-5- N-oxymethyl-amids erhalten werden. Sie stellt ein farbloses Pulver dar, das keinen scharfen Schmelzpunkt zeigt, sondern sieh beim Erwär men langsam zersetzt.
Die Salze der neuen Verbindung sind sehr beständig. Ihre wässerigen Lösungen reagie ren nahezu neutral und sind für Injektionen vorzüglich geeignet.
Die neue Verbindung lässt sieh beispiels weise leicht in Form ihrer Salze, z. B. des Natriums, Kalziums, oder von Aminen, wie von Diäthylamin, Diäthanolamin, Morpholin usw., isolieren. Zu diesem Zwecke kann man, wie im Beispiel näher beschrieben, das dem verwendeten alkalischen Kondensationsmittel entsprechende Salz durch Vermischen der Reaktionslösung mit einer organischen, mit Vrasser mischbaren Lösungsmittel ausfällen.
Process for the preparation of a new aldehyde derivative The subject of the patent is a process for the preparation of a new aldehyde derivative which has good germicidal properties. The compound and mainly its soluble salts are intended to be used to combat infectious diseases.
The method forming the subject of the patent is characterized in that pyridine-2,5-dicarboxylic acid-5-amide formaldehyde is allowed to act, with the pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide being formed. The formaldehyde can, for example, a formaldehyde-yielding connec tion, z. B. a polymeric formaldehyde (triozymethylene, paraformaldehyde), men entstam. The reaction is preferably carried out in an alkaline medium, since undesirable by-products are easily formed when working below pH 7.
<I> Example </I> 200 g of pyridine-2,5-dicarboxylic acid-5-amide are slurried in 600 cm3 of water and dilute sodium hydroxide solution 1:10 to p = 9 is added with stirring. The mixture is heated to 80 on the water bath and stirred with 450 cm3 of 361 / o aqueous formaldehyde solution. It is held at 80 for 15 minutes and the hydrogen ion concentration is adjusted to a value of 9-10 using sodium hydroxide solution. Then activated charcoal is added, filtered and neutralized with formic acid exactly to p $ 7. Then acetone is stirred in until a precipitate is formed.
The same is filtered off with suction after 24 hours and washed with acetone. By vacuum drying at 30 to 40, the sodium salt of pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide is obtained as a colorless powder which dissolves up to 20% in cold water with a practically neutral reaction.
The sodium salt obtained in this way can very easily be precipitated from water with the aid of acetone.
The free compound can be obtained by carefully acidifying the aqueous solution of a salt of pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide. It is a colorless powder that does not show a sharp melting point, but rather slowly decomposes when heated.
The salts of the new compound are very stable. Your aqueous solutions react almost neutrally and are ideally suited for injections.
The new compound can see example, easily in the form of their salts, eg. B. of sodium, calcium, or amines, such as diethylamine, diethanolamine, morpholine, etc. isolate. For this purpose, as described in more detail in the example, the salt corresponding to the alkaline condensing agent used can be precipitated by mixing the reaction solution with an organic solvent miscible with Vrasser.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH266516T | 1948-05-20 | ||
| CH315083T | 1953-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH315083A true CH315083A (en) | 1956-07-15 |
Family
ID=25730908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH315083D CH315083A (en) | 1948-05-20 | 1953-04-25 | Process for the preparation of a new aldehyde derivative |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH315083A (en) |
-
1953
- 1953-04-25 CH CH315083D patent/CH315083A/en unknown
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