CH269089A - Process for the preparation of a new aldehyde derivative. - Google Patents

Process for the preparation of a new aldehyde derivative.

Info

Publication number
CH269089A
CH269089A CH269089DA CH269089A CH 269089 A CH269089 A CH 269089A CH 269089D A CH269089D A CH 269089DA CH 269089 A CH269089 A CH 269089A
Authority
CH
Switzerland
Prior art keywords
preparation
soluble
benzoic acid
formaldehyde
aldehyde derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
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
Application filed by Cilag Ag filed Critical Cilag Ag
Publication of CH269089A publication Critical patent/CH269089A/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, 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
    • A01N37/44Biocides, 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

Description

       

  Verfahren     zur    Darstellung     eines    neuen     Aldehydderivates.       Gegenstand der Erfindung ist ein Verfah  ren zur Herstellung     eines    neuen Abkömm  lings eines     Aldehydes,    welcher gute keim  tötende Eigenschaften     besitzt.    Er soll als  Desinfektionsmittel und in Form seiner  löslichen     Salze    zur Bekämpfung von Infek  tionskrankheiten verwendet werden.  



  Das Verfahren ist dadurch gekennzeichnet,  dass man     p-Formyl-amino-benzoesäure    auf  Formaldehyd einwirken lässt, wobei sich die       p-(N-Formyl-oxymethylamino)        -benzoesäure     bildet. Der Formaldehyd kann beispielsweise  einer in Gegenwart der     p-Formylamino-          benzoesäure    Formaldehyd liefernden Verbin  dung, z. B. einem polymeren Formaldehyd       (Trioxymethylen,        Paraformaldehyd    usw.) ent  stammen.  



       Beispiel:     Eine Mischung von 19 g     p-Formylamino-          benzoesäure,    58     em3        2n-Kalilauge    und 10     cm3     40     o/oiger        Formaldehydlösung    wird eine halbe  Stunde bei Zimmertemperatur geschüttelt.  Darauf wird unter     Umrühren    so lange auf  80-90  C erwärmt, bis eine klare Lösung ent  standen ist, und diese filtriert.

   Beim Erkalten  der in heissem Zustande auf ein,     pu    von 5 ge  brachten Lösung     kristallisiert    die p-     (N-Formyl-          oxymethylamino)-benzoesäure    aus.  



  Die neue     Karbonsäure    ist in     Alkalien        und     in Lösungen von Aminen leicht löslich, wenig  löslich in     Alkohol    und schwer     löslich    in Was  ser, Äther, Chloroform und Benzol.    Sie besitzt schon bei     Zimmertemperatur     grosse Neigung, sich zu zersetzen. Bei höherer  Temperatur erfolgt diese Umwandlung so  rasch, dass ,der Schmelzpunkt der beschriebe  nen Säure nicht ermittelt werden kann.  



  Beständig sind dagegen die Salze der  neuen Säure. Ihre     wässrigen    Lösungen reagie  ren     nahezu-neutral    und sind für Injektionen  vorzüglich geeignet.  



  Die gebildete neue     Karbonsäure    lässt sich  auch in Form ihrer Salze, z. B. des Natriums,  Kalziums, oder als Salze von Aminen, wie       Diäthylamin,        Diäthanolamin,        Morpholin    iso  lieren. Zu diesem Zweck kann man beim Ar  beiten gemäss dem Beispiel das Ansäuern des  Reaktionsgemisches     unterlassen;    das dem ver  wendeten     alkalischen        Kondensationsmittel    ent  sprechende     Salz        wird        dann    direkt und in  nahezu     quantitativer    Ausbeute erhalten.



  Process for the preparation of a new aldehyde derivative. The invention relates to a method for producing a new descendant of an aldehyde which has good germicidal properties. It is to be used as a disinfectant and in the form of its soluble salts to combat infectious diseases.



  The method is characterized in that p-formylamino-benzoic acid is allowed to act on formaldehyde, p- (N-formyl-oxymethylamino) -benzoic acid being formed. The formaldehyde can, for example, a compound providing formaldehyde in the presence of p-formylamino benzoic acid, e.g. B. a polymeric formaldehyde (trioxymethylene, paraformaldehyde, etc.) come ent.



       Example: A mixture of 19 g of p-formylaminobenzoic acid, 58 cubic meters of 2N potassium hydroxide solution and 10 cm3 of 40% formaldehyde solution is shaken for half an hour at room temperature. The mixture is then heated to 80-90 ° C. with stirring until a clear solution is formed, and this is filtered.

   When the hot solution cools to one pu of 5, the p- (N-formyl oxymethylamino) benzoic acid crystallizes out.



  The new carboxylic acid is easily soluble in alkalis and in solutions of amines, slightly soluble in alcohol and sparingly soluble in water, ether, chloroform and benzene. Even at room temperature it has a great tendency to decompose. At a higher temperature, this conversion takes place so quickly that the melting point of the acid described cannot be determined.



  In contrast, the salts of the new acid are stable. Your aqueous solutions react almost neutrally and are ideally suited for injections.



  The new carboxylic acid formed can also be in the form of its salts, e.g. B. of sodium, calcium, or as salts of amines such as diethylamine, diethanolamine, morpholine iso lieren. For this purpose you can refrain from acidifying the reaction mixture when working according to the example; the salt corresponding to the alkaline condensing agent used is then obtained directly and in almost quantitative yield.


    

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Derivates eines Aldehydes, dadurch gekenn zeichnet, dass man p-Formylamino-benzoe- säure auf Formaldehyd einwirken lässt, wobei sich die p- (N-Formyl-oxymethylamino)- benzoesäure bildet. Das Verfahrensprodukt stellt ein farbloses mikrokristallines Pulver dar, das keinen definierten Schmelzpunkt be sitzt, sondern sich beim Erwärmen zersetzt. PATENT CLAIM: Process for the preparation of a new derivative of an aldehyde, characterized in that p-formylamino-benzoic acid is allowed to act on formaldehyde, with p- (N-formyl-oxymethylamino) -benzoic acid being formed. The process product is a colorless, microcrystalline powder that does not have a defined melting point, but instead decomposes when heated. Es ist schwer löslich in Wasser, Äther, Chloroform und Benzol und wenig löslich in Alkohol. In verdünnten Alkalien und in Lö sungen von Aminen ist es leicht löslich. Es soll als Desinfektionsmittel und in Form seiner löslichen Salze zur Bekämpfung von Infektionskrankheiten Verwendung fin den. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in alkalischem Milieu vornimmt. It is sparingly soluble in water, ether, chloroform and benzene and sparingly soluble in alcohol. It is easily soluble in dilute alkalis and in solutions of amines. It is intended to be used as a disinfectant and in the form of its soluble salts for combating infectious diseases. SUBCLAIM: Process according to claim, characterized in that the reaction is carried out in an alkaline medium.
CH269089D 1948-05-20 1948-05-20 Process for the preparation of a new aldehyde derivative. CH269089A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH266516T 1948-05-20
CH269089T 1948-05-20

Publications (1)

Publication Number Publication Date
CH269089A true CH269089A (en) 1950-06-15

Family

ID=25730896

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269089D CH269089A (en) 1948-05-20 1948-05-20 Process for the preparation of a new aldehyde derivative.

Country Status (1)

Country Link
CH (1) CH269089A (en)

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