CH237503A - Process for the preparation of 4-amino-benzene-sulfonylaminomethanesulfonic acid. - Google Patents

Process for the preparation of 4-amino-benzene-sulfonylaminomethanesulfonic acid.

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Publication number
CH237503A
CH237503A CH237503DA CH237503A CH 237503 A CH237503 A CH 237503A CH 237503D A CH237503D A CH 237503DA CH 237503 A CH237503 A CH 237503A
Authority
CH
Switzerland
Prior art keywords
acid
sulfonylaminomethanesulfonic
amino
benzene
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Asklepia
Original Assignee
Ag Asklepia
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 Ag Asklepia filed Critical Ag Asklepia
Publication of CH237503A publication Critical patent/CH237503A/en

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Classifications

    • 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)

Description

       

  Verfahren zur Herstellung von     4-Amino-benzol-sulfonylaminomethansulfonsäur    e.    Es wurde gefunden, dass die bisher     un-          bekannte        4-Amino-benzel-sulfonylamino-          methansulfansäure    leicht dadurch hergestellt  werden kann, dass man die     Phenyl-l-amino-          methansulfonsäure    - 4 -     sulfonylaminomethan-          sulfonsäure    -der Formel       HSO@    .     CH,.        NH.        CH,.    SO,.

       NH.        CH-    S0311  mit milden     Verseifungsmitteln    behandelt, so  dass nur der an der kernständigen     Amino-          gruppe    befindliche     Methansulfonsäurerest     abgespalten wird. Dies gelingt zum Beispiel  durch kurzes Erhitzen mit     n-Salzsäure.     



  Die neue     Sulfonsäure,    deren Alkali- und       Erdalkalisalze    ziemlich gut wasserlöslich  sind, wirkt stark bakterizid und ist gleich  zeitig weitgehend ungiftig; ihre Salzlösung       eignet    sich     wegen    ihrer Reizlosigkeit hervor  ragend zur Injektion. Die Säure kristallisiert  in farblosen Plättchen, die bei 210  schmel  zen, sie ist schwer löslich in Wasser und  unlöslich in organischen Lösungsmitteln.

   Das       Natriumsalz    der     Sulfonsäure    kristallisiert in    farblosen Nadeln mit einem Zersetzungspunkt  von 245 ; die     wässrige    Lösung des     Natrium-          salzes    hat ein PH von 5,5.  



  <I>Beispiel:</I>  90 g     Phenyl-l-aminomethansulfonsäure-          4-sulfonylaminomethansulfonsäure    oder 100 g  des     Di-Natriumsalzes    dieser Säure (hergestellt  aus 1     Mol-4-Amino-benzalsulfänamid    und  2 Mal     Formaldelhydnatriumbisulfit)    werden  in Wasser gelöst, auf ein Volumen von  750 cm' aufgefüllt und zum Sieden erhitzt.  In die kochende Lösung werden dann 750 cm'  2     n-Salzsäure    ebenfalls siedend heiss einge  gossen und die Lösung dann noch etwa 1/2 Mi  nute gekocht.

   Nach mehrtägigem Stehen in  der Kälte wird die kristallinisch     abgescUie-          dene        4-Amino-benzol-sulfonylaminamethan-          sulfonsäure    abgesaugt. Ausbeute: 20 g =  30 % der Theorie. Die schwach rosa gefärbten  Kristalle zeigen nach zweimaligem     Umkri-          stallisieren    aus Wasser unter Zusatz von  Tierkohle .den F.     210     (Mikro).



  Process for the preparation of 4-amino-benzene-sulfonylaminomethanesulfonic acid e. It has been found that the previously unknown 4-amino-benzel-sulfonylamino-methanesulfanic acid can easily be prepared by adding the phenyl-1-aminomethanesulfonic acid - 4 - sulfonylaminomethanesulfonic acid - of the formula HSO @. CH ,. NH. CH ,. SO,.

       NH. CH-S0311 treated with mild saponifying agents so that only the methanesulfonic acid residue on the nucleus amino group is split off. This can be done, for example, by briefly heating with n-hydrochloric acid.



  The new sulfonic acid, the alkali and alkaline earth salts of which are fairly soluble in water, has a strong bactericidal effect and is at the same time largely non-toxic; Their saline solution is ideal for injection because of its lack of irritation. The acid crystallizes in colorless platelets that melt at 210, it is sparingly soluble in water and insoluble in organic solvents.

   The sodium salt of sulfonic acid crystallizes in colorless needles with a decomposition point of 245; the aqueous solution of the sodium salt has a pH of 5.5.



  <I> Example: </I> 90 g of phenyl-l-aminomethanesulfonic acid-4-sulfonylaminomethanesulfonic acid or 100 g of the disodium salt of this acid (prepared from 1 mol-4-amino-benzalsulfanamide and 2 times formaldehyde sodium bisulfite) are dissolved in water, made up to a volume of 750 cm 'and heated to the boil. 750 cm '2 N hydrochloric acid is then poured into the boiling solution, likewise boiling hot, and the solution is then boiled for about 1/2 minute.

   After standing in the cold for several days, the crystalline 4-amino-benzene-sulfonylamine-methanesulfonic acid is filtered off with suction. Yield: 20 g = 30% of theory. The pale pink colored crystals show after two recrystallization from water with the addition of animal charcoal the F. 210 (micro).

Claims (1)

PATENTANSPRÜCH: Verfahren zur Herstellung von 4-Amino- benzol-sulfonylaminomethansulfonsäure, da durch gekennzeichnet, dass man Phenyl-l aminomethansulfonsäure-4-sulfonylaminome- thansulfonsäure schonend verseift. Die neue Sulfonsäure kristallisiert in farblosen Plättchen, die bei 210" schmelzen. Sie ist schwer löslich in Wasser und unlös lich in organischen Lösungsmitteln. PATENT CLAIM: Process for the production of 4-aminobenzene-sulfonylaminomethanesulfonic acid, characterized in that phenyl-1-aminomethanesulfonic acid-4-sulfonylaminomethanesulfonic acid is gently saponified. The new sulfonic acid crystallizes in colorless flakes that melt at 210 ". It is sparingly soluble in water and insoluble in organic solvents. Das Natriumsalz der Sulfonsäure kristalli- siert in farblosen Nadeln mit einem Zer setzungspunkt von \?45"; die wässrige Lösung des Natriumsalzes hat ein PH von 5,5. The sodium salt of sulfonic acid crystallizes in colorless needles with a decomposition point of 45 "; the aqueous solution of the sodium salt has a pH of 5.5.
CH237503D 1941-05-29 1941-09-02 Process for the preparation of 4-amino-benzene-sulfonylaminomethanesulfonic acid. CH237503A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE237503X 1941-05-29

Publications (1)

Publication Number Publication Date
CH237503A true CH237503A (en) 1945-04-30

Family

ID=5903125

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237503D CH237503A (en) 1941-05-29 1941-09-02 Process for the preparation of 4-amino-benzene-sulfonylaminomethanesulfonic acid.

Country Status (1)

Country Link
CH (1) CH237503A (en)

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