CH212358A - 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
CH212358A
CH212358A CH212358DA CH212358A CH 212358 A CH212358 A CH 212358A CH 212358D A CH212358D A CH 212358DA CH 212358 A CH212358 A CH 212358A
Authority
CH
Switzerland
Prior art keywords
water
sulfonic acid
acid amide
acid
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 CH212358A publication Critical patent/CH212358A/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

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

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 Darstellung einer wasser  löslichen     Sulfonsäureamidverbindung,    das da  durch     gekennzeichnet    ist, dass man     auf        4-          Amino    - 2     -methyl-5-methogybeuzolsulf        onamid     eine     Halogensulfonsäure,    vorzugsweise     Chlor-          sulfonsäure,

          einwirken    lässt und das ge  bildete     4-Sulfamino-2-methyl-5-methogy-ben-          zolsulfonamid    in Form des     Natriumsalzes    ab  scheidet. Die Umsetzung erfolgt zweckmässig  in     Gegenwart    eines tertiären Amins,     wie    Py-         ridin,        Chinolin    oder     Dialkylanilin;    sie kann  auch mit Hilfe anorganischer säurebindender  Mittel, z.

   B.     Calciumcarbonat,        Natriumbicar-          bonat,        Magnesiumcarbonat    oder     Alkaliphos-          phat,        sowie    in Gegenwart eines indifferenten  Lösungsmittels, wie Benzol,     Toluol,    Schwe  felkohlenstoff oder Äther durchgeführt wer  den.     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-          Sulfamino-    2     -methyl-5-methogybenzolsulf        on-          amids    bildet     färblose    Kristalle, die in Wasser  leicht löslich sind. Das neue Produkt soll  therapeutische     Anwendung    finden.

      <I>Beispiel:</I>  In 300 cm' mit     Eis-Natriumchlorid-          mischung    gekühltes     Pyridin    lässt man     unter         Rühren 58 g     Chlorsulfonsä.ure        eintropfen.    Zu  der weissen     Reaktionsmischunb    gibt man  108     g        4-Amino-2-methyl-5-methoxybenzolsul-          fonamid    und erhitzt eine Stunde auf dem  Wasserbad. Man fügt 200 cm'     40%i-,e    Na  tronlauge hinzu und destilliert das     Pyridin     mit Wasserdampf ab.

   Nach Behandeln mit  Tierkohle saugt man ab, versetzt die     Lösung     mit     Natriumchlorid    und fällt mit     Ammo-          niumchlorid.    worauf das     Natriumsalz    des 4       Sulfamino-?-methyl-5-methoxi--benzolsulfon-          amids    als     weisser        Kristallbrei    ausfällt. Aus  verdünntem Methylalkohol oder verdünnter       I\Tatriumchloridlösunb    umkristallisiert erhält  man die genannte Verbindung in Form farb  loser Kristalle, die in Wasser leicht löslich       sind.    -



  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 added to 4-amino-2-methyl-5-methogybeuzolsulfonamide

          Let it take effect and the 4-sulfamino-2-methyl-5-methogybenzenesulfonamide formed separates out 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 with the help of inorganic acid-binding agents, e.g.

   B. calcium carbonate, sodium bicarbonate, magnesium carbonate or alkali metal phosphate, as well as in the presence of an inert solvent such as benzene, toluene, carbon sulfur 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-sulfamino-2-methyl-5-methogybenzenesulfonamide thus obtainable forms colorless crystals which are easily soluble in water. The new product should find therapeutic application.

      <I> Example: </I> In 300 cm of pyridine cooled with an ice-sodium chloride mixture, 58 g of chlorosulphonic acid are added dropwise with stirring. 108 g of 4-amino-2-methyl-5-methoxybenzenesulfonamide are added to the white reaction mixture and the mixture is heated on a water bath for one hour. 200 cm '40% i-, e sodium hydroxide solution is added and the pyridine is distilled off with steam.

   After treatment with animal charcoal, the solution is filtered off with suction, sodium chloride is added and the solution is precipitated with ammonium chloride. whereupon the sodium salt of 4 sulfamino -? - methyl-5-methoxy - benzenesulfonamide precipitates as a white crystal paste. Recrystallized from dilute methyl alcohol or dilute sodium chloride solution, the compound mentioned is obtained in the form of colorless crystals which are easily soluble in water. -

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung einer wasser löslichen Sulfonsäureamidverbindunb, da durch gekennzeichnet, dass man auf 4-Amino- 2 - methyl - 5 - methoxybenzolsulfonamid eine Halogensulfonsäure einwirken lässt und das gebildete 4-Sulfamino-?-methyl-5-methoxy- benzolsulfonamid in Form des Natriumsalzes abscheidet. PATENT CLAIM A process for the preparation of a water-soluble sulfonic acid amide compound, characterized in that a halosulfonic acid is allowed to act on 4-amino-2-methyl-5-methoxybenzenesulfonamide and the 4-sulfamino-? Sodium salt separates. Das so erhältliche Natriumsalz des 4-Sulf- amin o - 2 -methyl-5-methoxyben.zolsulfona.mids bildet farblose Kristalle, die in Wasser leicht. löslieh sind. I \ TER -)#\ SPRACHE 1. Verfahren nach Patentanspruch, dadurch Ol ekennzeiehnet, dass die Umsetzung in Gegenwart eines säurebindenden Mittels erfolgt. ?. Verfahren naeh Patentanspruch und Un teranspruch 1, dadurch gekennzeichnet. The thus obtainable sodium salt of 4-sulfamine o - 2 -methyl-5-methoxyben.zolsulfona.mids forms colorless crystals, which in water easily. are soluble. I \ TER -) # \ LANGUAGE 1. Process according to patent claim, characterized in that the reaction takes place in the presence of an acid-binding agent. ?. Method according to patent claim and sub-claim 1, characterized. dass die L: msetzun-- in Gegenwart von überschüssigem Pyridin erfolgt. 3. Verfahren nach Patentanspruch, dadurch 0;elzennzeichnet, dass als Halogensulfon- säure Chlorsulfonsäure verwendet wird. that the L: msetzun-- takes place in the presence of excess pyridine. 3. The method according to claim, characterized in that chlorosulfonic acid is used as the halosulfonic acid.
CH212358D 1937-09-08 1938-08-25 Process for preparing a water-soluble sulfonic acid amide compound. CH212358A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE212358X 1937-09-08
CH207607T 1938-08-25

Publications (1)

Publication Number Publication Date
CH212358A true CH212358A (en) 1940-11-15

Family

ID=25724431

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212358D CH212358A (en) 1937-09-08 1938-08-25 Process for preparing a water-soluble sulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH212358A (en)

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