CH212360A - Process for preparing a water-soluble sulfonic acid amide compound. - Google Patents

Process for preparing a water-soluble sulfonic acid amide compound.

Info

Publication number
CH212360A
CH212360A CH212360DA CH212360A CH 212360 A CH212360 A CH 212360A CH 212360D A CH212360D A CH 212360DA CH 212360 A CH212360 A CH 212360A
Authority
CH
Switzerland
Prior art keywords
water
acid
sulfonic acid
acid amide
amide compound
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH212360A publication Critical patent/CH212360A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Description

  

  Verfahren zur Darstellung einer wasserlöslichen     Sulfonsäureamidverbindung.       Wie im Hauptpatent angegeben ist, erhält  man in Wasser leicht und neutral lösliche,  bakterizid hoch wirksame     Verbindungen,          wenn    man     Benzolsulfonsäureamidverbindun-          gen    herstellt, die in     p-Stellung    zur     Sulfon-          säureamidgruppe    durch das     Stickstoffatom     einer stickstoffhaltigen Gruppe     substituiert     sind, und die mindestens dann,

       wenn    jene       stickstoffhaltige    Gruppe nicht eine     Sulfamin-          säuregruppe        ist,    eine     Sulfaminsäuregruppe     über einen organischen Rest gebunden ent  halten.  



  Gegenstand des vorliegenden Patentes, ist  ein Verfahren zur Herstellung einer wasser  löslichen     Sulfonsäureamidverbindung,    das da  durch     gekennzeichnet    ist, dass man auf     4-(4'-          Aminobenzylamino)    -     benzolsulfonamid        eine          Halogensulfonsäure,    .vorzugsweise     Chlorsul-          fonsäure,    einwirken lässt und das     gebildete     4 - (4' -     Sulfaminobenzylamino)

          -benzolsulfon-          amid    in Form des     Natriumsalzes    abscheidet.  Die Umsetzung erfolgt zweckmässig in Ge  genwart eines tertiären Amins, wie     Pyridin,            Chinolin    oder     Dialkylanilin,    sie kann auch  mit Hilfe anorganischer säurebindender Mit  tel, z.

   B.     Calciumcarbonat,        Natriumbicarbo-          nat,        Magnesiumcarbonat    oder     Alkaliphosphat     sowie in Gegenwart eines indifferenten Lö  sungsmittels, wie Benzol,     Toluol,    Schwefel  kohlenstoff oder Äther     durchgeführt    werden.       Im.    Überschuss angewendet,     können    auch die  tertiären Amine als Lösungsmittel dienen.  An Stelle der freien     Halogensulfonsäure     können auch deren     Anlagerungsprodukte    an  tertiäre     Amine,    wie z.

   B.     Pyridin,        Chinolin     oder     Dialkylaniline,    verwendet werden.  



  Das so erhältliche     Natriumsalz    des  4 - (V-     Sulfaminobenzylamino)    -     benzolsulfon-          amids    bildet farblose, in Wasser neutral lös  liche     Kristalle.    Das neue Produkt soll thera  peutische Anwendung finden.  



  <I>Beispiel:</I>  In das     Reaktionsgemisch    von 200     ein'        Py-          ridin    und 24 g     Chlorsulfonsäure    trägt man  55 g 4-(4'-Aminobenzylamino)-benzolsulfon-           amid    ein und erhitzt eine Stunde auf dem       Wasserbad.    Nach dieser Zeit versetzt man  die Reaktionslösung mit 80 cm' 40     ',ö        iger     Natronlauge und destilliert das     Pyridin    mit  Wasserdampf ab.

   Nach Reinigung des Rück  standes mit Tierkohle saugt man ab, versetzt  das Filtrat mit     Natriumchlorid    und fällt       mit        Ammoniumehlorid    das     Natriumsalz    des  4 - (4' -     Sulfaminobenzylamino)        -benzolsulfon-          amids.    Es wird aus     Natriumchloridlösung    in       Form    farbloser     Kristalle    erhalten, die sich in  Wasser neutral lösen.



  Process for preparing a water-soluble sulfonic acid amide compound. As stated in the main patent, compounds which are easily and neutrally soluble in water and have a high bactericidal activity are obtained if benzene sulfonic acid amide compounds are prepared which are substituted in the p-position to the sulfonic acid amide group by the nitrogen atom of a nitrogen-containing group, and which are at least

       when that nitrogen-containing group is not a sulfamic acid group, a sulfamic acid group is bonded through an organic residue.



  The subject of the present patent is a process for the preparation of a water-soluble sulfonic acid amide compound, which is characterized in that a halosulfonic acid, preferably chlorosulfonic acid, is allowed to act on 4- (4'-aminobenzylamino) benzenesulfonamide and the 4 - (4 '- sulfaminobenzylamino)

          -benzenesulfonamide separates in the form of the sodium salt. The reaction is expediently carried out in the presence of a tertiary amine such as pyridine, quinoline or dialkylaniline, it can also tel with the help of inorganic acid-binding agents, eg.

   B. calcium carbonate, sodium bicarbonate, magnesium carbonate or alkali metal phosphate and in the presence of an inert solvent such as benzene, toluene, carbon disulfide or ether. If used in excess, the tertiary amines can also serve as solvents. Instead of the free halosulfonic acid, its addition products with tertiary amines, such as.

   B. pyridine, quinoline or dialkylanilines can be used.



  The sodium salt of 4- (V-sulfaminobenzylamino) - benzenesulfonamide which can be obtained in this way forms colorless crystals which are neutral in water. The new product is intended to be used therapeutically.



  <I> Example: </I> 55 g of 4- (4'-aminobenzylamino) benzenesulfonamide are added to the reaction mixture of 200 a pyridine and 24 g of chlorosulfonic acid and heated on a water bath for one hour. After this time, the reaction solution is mixed with 80 cm of '40' sodium hydroxide solution and the pyridine is distilled off with steam.

   After cleaning the residue with animal charcoal, the filtrate is filtered off with suction, sodium chloride is added and the sodium salt of 4 - (4 '- sulfaminobenzylamino) benzenesulfonamide is precipitated with ammonium chloride. It is obtained from sodium chloride solution in the form of colorless crystals which dissolve neutrally in water.

Claims (1)

\ PATENTANSPRUCH: Verfahren zur Herstellung einer wasser löslichen Sulfonsäureamidverbindung, dadurch gekennzeichnet, dass man auf 4-(4' A.mino- benzylamino)-benzolsulfonamid eine Halogen- sulfonsäure einwirken lässt und das gebildete 4 - (4' - Sulfaminobenzylamino) -benzolsulfon- amid in Form des Natriumsalzes abscheidet.. \ PATENT CLAIM: Process for the production of a water-soluble sulfonic acid amide compound, characterized in that a halosulfonic acid is allowed to act on 4- (4 'A.mino-benzylamino) -benzenesulfonamide and the 4 - (4' - sulfaminobenzylamino) -benzenesulfone- amide in the form of the sodium salt. Das so erhältliche Nat-iumsalz des 4 - (4' - ,Sulfaniinobenzylaiiiitio) - benzolsulfon- a.mids bildet farblose. in Wasser neutral lös liche Kristalle. UN TER AN SPRtrCHE 1.. Verfahren nach. Patentanspruch, dadurch gekennzeichnet. dass die Umsetzung in Ge- genwa.rt. eines säurebindenden Mittels er folgt. The sodium salt of 4 - (4 '-, sulfaniinobenzylaiiiitio) - benzenesulfone a.mide thus obtainable forms colorless. Crystals that are neutrally soluble in water. UNDER LANGUAGE 1 .. Procedure according to. Patent claim, characterized. that the implementation in the present. an acid-binding agent he follows. 3. Verfahren nach Patentanspruch und Un teranspruch 1., dadurch gekennzeichnet, dass die Umsetzung in Gegenwart von überschüssigem Pyridin erfolgt. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass als Halogenstilfon- säure Chlorsulfonsäure verwendet wird. 3. The method according to claim and un terclaim 1., characterized in that the reaction takes place in the presence of excess pyridine. 3. The method according to claim, characterized in that chlorosulfonic acid is used as the halostilfonic acid.
CH212360D 1937-09-08 1938-08-25 Process for preparing a water-soluble sulfonic acid amide compound. CH212360A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE212360X 1937-09-08
CH207607T 1938-08-25

Publications (1)

Publication Number Publication Date
CH212360A true CH212360A (en) 1940-11-15

Family

ID=25724433

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212360D CH212360A (en) 1937-09-08 1938-08-25 Process for preparing a water-soluble sulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH212360A (en)

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