DE833041C - Process for the preparation of sulfosalicylates of p-aminobenzenesulfonamide - Google Patents

Process for the preparation of sulfosalicylates of p-aminobenzenesulfonamide

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Publication number
DE833041C
DE833041C DEP6600D DEP0006600D DE833041C DE 833041 C DE833041 C DE 833041C DE P6600 D DEP6600 D DE P6600D DE P0006600 D DEP0006600 D DE P0006600D DE 833041 C DE833041 C DE 833041C
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DE
Germany
Prior art keywords
solution
sulfo
sulfosalicylates
preparation
indicates
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEP6600D
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German (de)
Inventor
Dr Werner Ursum
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vial & Uhlmann Inh Apoth E Rat
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Vial & Uhlmann Inh Apoth E Rat
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Filing date
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Application filed by Vial & Uhlmann Inh Apoth E Rat filed Critical Vial & Uhlmann Inh Apoth E Rat
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Publication of DE833041C publication Critical patent/DE833041C/en
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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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Sulfosalicylaten des p-Aminobenzolsulfonamids Nach einem bekannten Vorschlag soll p-Am.inobenzolsulfonam.i,d-sulfosalicylat derart hergestellt werden, :daß die Komponenten in sehr verdünnter wäßriger bzw. alkoholischer Lösung aufeinander einwirken gelassen werden und die :stark verdünnte Lösung nach Beendigung der Reaktion bei niedrigen Temperaturen im Vakuum auf eine für die Weiterverarbeitung @geeignete Konzentration gebracht wird. Diese Vorschrift steht im Einklang mit der Literatur, in der mehrfach angegeben ist, daß p-Aminobenzol-sülfonamid-sulfosalicylat in wäßriger Lösung zur Zersetzung neigt und infolgedessen die Einwirkung höherer Temperaturen auf derartige Lösungen zu vermeiden sei. Das bekannte vorstehend angegebene Verfahren, bei dem in stark verdünnter Lösung gearbeitet wird und die Lösung alsdann wieder unter milden Bedingungen im Vakuum konzentriert werden muß, ;ist umständlich und für die Gewinnung der Verbindung in technischem Maßtstab nicht geeignet. Größere Substanzmengen können nach diesem bekannten Verfahren nur unter großen Schwierigkeiten erhalten werden.Process for the preparation of sulfosalicylates of p-aminobenzenesulfonamide According to a known proposal, p-Am.inobenzolsulfonam.i, d-sulfosalicylate should be such be prepared: that the components in very dilute aqueous or alcoholic Solution can be allowed to act on each other and the: strongly diluted solution after Completion of the reaction at low temperatures in a vacuum on one for further processing @suitable concentration is brought. This requirement is in line with the Literature in which it is stated several times that p-aminobenzene sulfonamide sulfosalicylate tends to decompose in aqueous solution and, as a result, the effect is higher Temperatures on such solutions should be avoided. The known above Process in which one works in a very dilute solution and then the solution must be concentrated again under mild conditions in a vacuum; is cumbersome and not suitable for obtaining the connection on a technical scale. Bigger ones According to this known process, amounts of substance can only be achieved with great difficulty can be obtained.

Nach vorliegender Erfindung gelingt die Herstellung von p-Am.inobenzolsulfonarni,d-sulfosa!licylat in überraschend einfacher Weise, und zwar ,dadurch, daß man im Gegensatz zu oder bisher herrschenden Meinung die Komponenten in konzentrierter Lösung in der Hitze, z. B. bei Temperaturen von etwa 8o bis ioo° aufeinander wirken läßt.According to the present invention, p-Am.inobenzolsulfonarni, d-sulfosa! Licylat can be prepared in a surprisingly simple way, namely, by contrasting with or the prevailing opinion so far, the components in concentrated solution in the heat, z. B. can act on each other at temperatures of about 8o to ioo °.

In Ausübung der Erfindung kann man z. B. derart verfahren, d'aß 15 kg Sulfosalicyd@säure in 33 kg Wassergelöst werden und @i.n die auf 9o° erwärmte Lösung io kg p-Aminobenzolsulfonami-d unter Aufrechterhaltung einer Temperatur von etwa 9o Ibis 95° eingetragen werden. Die erhaltene Lösung wird finit Zoo g Tierkohle versetzt und alsdann filtriert; leim Abkühlen kristallisiert p-Aminol>enzolsulfoiiainid-sulfosalicylat in großer Menge aus. Nach Absaugen und Auswaschen finit etwa 51 kaltem Wasser erhält man die @'erbinduirg mit einer AuslieUte voll 2o kg Substanz.In exercising the invention you can, for. B. proceed in such a way that 15 kg of sulfosalicyd @ acid are dissolved in 33 kg of water and io kg of p-aminobenzene sulfonamides are entered into the solution heated to 90 ° while maintaining a temperature of about 90 ° at 95 °. The resulting solution is finely mixed with zoo g of animal charcoal and then filtered; p-aminol> enzolsulfoiiainid-sulfosalicylat crystallizes out in large quantities when it cools. After suctioning off and washing out finitely about 51 cold water, the compound is obtained with an outlet full of 20 kg of substance.

Das Verfahren zeichnet sich durch außerordentliche Einfachheit und sehr ;große Ausbeuten aus. l:in besorbderer Vorzug liegt noch darin, daß das nach vorliegender Erfindung gewonnene p-Amino-1ietizolsulfonamid-sulfosalicylat unmittelbar in völlig reiner Form gewonnen ,@»ird. Dies geht u. a. daraus hervor, daß die nach vorstehendem Beispiel gewonnene Verbindung einen höheren SchmeIzpunkt zeigt als die nach dem bekannten Verfahren aus verdünnter Lösung gewonnene Verbindung und elaß dieser Schmelzpunkt (237') .durch mehrinaliges Umkristallisieren @in keiner Weise mehr geändert wird. Das p-Aminobenzolsulfonainidsulfosalicylat ist therapeutisch :außerordentlich wichtig. Die Gewinnung ,dieser wertvollen Verbiti-,dung durch ein sehr einfaches Verfahren mit überraschend hohen Ausbauten in unmittelbar reiner, gebrauchsfähiger .Form bedeutet einen großen Fortschritt. Der Erfolg war im Hinblick auf die aus der Literatur zu entnehmende Zersetz1ichkeit von p-:\minobenzolsulfonami,d in wäßriger Lösung und die Tatsache, daß das bekannte Verfahren zur Verstellung der Verbindung ausdrücklich das Arbeiten in stark verdünnter Lösung vorschreibt und das umständliche .und zeitraubende Konzentrieren der .wäßrigen Lösung im Vakuum in Kauf nimmt, in keiner Weise vorauszusehen.The procedure is characterized by its extraordinary simplicity and very; large yields. l: The greater advantage lies in the fact that that after p-Amino-1ietizolsulfonamid-sulfosalicylat obtained directly according to the present invention obtained in completely pure form, @ »earth. This is inter alia. from the fact that the after Compound obtained in the above example shows a higher melting point than the compound obtained by the known method from dilute solution and This melting point (237 ') was not possible by repeated recrystallization in none Way more is changed. The p-aminobenzenesulfonainide sulfosalicylate is therapeutic : extremely important. The acquisition of this valuable association through a very simple process with surprisingly high extensions in directly pure, usable .form represents a great step forward. The success was in view on the decomposition of p -: \ minobenzolsulfonami, which can be taken from the literature, d in aqueous solution and the fact that the known method of adjustment the connection expressly prescribes working in a very dilute solution and the laborious and time-consuming concentration of the .aqueous solution in vacuo accepts not to foresee in any way.

Weitere Versuche haben ergeben, daß man in entsprechender Weise auch Sul,fosalicylate von Derivaten des p-Aminobenzolsulfonamids herstellen kann. So gelingt z. B. die Herstellung des Sulfosalicylats des p-Aminobenzolsulfonamidothiazols glatt und in guter Ausbeute, indem man das ge- nannte Derivat in heiße konzentrierte wä ßrige Lö- sung von Sulfosalicylsättre einträgt und die heiße Lösung zur Beendigung <per Reaktion einige Zeit auf einer Temperatur zwischen #,o und ioo" beläßt. Beim Abkühlen der Lösung scheidet sich das Stilfo- salicyl,at des p-.:\ininol>enz(->lsulf4)naniidotliiazols in reiner kristalliner Forin a1>. In entsprechender Weise lassen sich auch andere Sulfosalicylate, z. B. des 1>-.\tninol)etizolacetstilfon- amids und des p-=lniinolic-uzolstilfoianiidoliyridins gewinnen. Die erfindungsgeinä ß erhältlichen sulfosalicN-l- sauren Salze haben eine beachtliche Desinfektions- wirkung und zeichnen sich gegenüber den Aus- gangsstoffen durch leichte Löslichkeit in \Z'asser aus. Further experiments have shown that sulphosalicylates can also be prepared from derivatives of p-aminobenzenesulphonamide in a corresponding manner. So z. B. the preparation of the sulfosalicylate of p-aminobenzene sulfonamidothiazole smoothly and in good yield by called derivative in hot concentrated aqueous solution solution of sulfosalicylic saturation enters and the hot Solution to terminate <by reaction for some time left at a temperature between #, o and ioo ". When the solution cools down, the stilfo- salicyl, at des p-.:\ininol>enz(->lsulf4)naniidotliiazols in pure crystalline forin a1>. Others can be done in the same way Sulfosalicylates, e.g. B. des 1> -. \ Tninol) etizolacetstilfon- amides and des p- = lniinolic-uzolstilfoianiidoliyridins to win. The sulfosalicN-l- available according to the invention acid salts have a considerable disinfectant effect and stand out against the basic substances due to their easy solubility in water the end.

Claims (1)

PATENTANSf'Rl`CHE: i. Verfahren zur Herstellung von Sulfo- salicylaten des p-Aniinobenzolsulfonaini@ds und seiner Derivate durch Aufeinanderwirken der Komponenten in wäßriger Lösung, @dadurch ge- kennzeichnet, daß die Unisetzung in konzen- trierter Lösung in der Hitze, z. B. bei etwa 8o bis ioo', vorzugsweise 9o bis 95', vorgenom- men wird. 2. Verfahren nach Anspruch i, dadurch ge- kennzeichnet, daß in eine konzentrierte, auf etwa 8o bis ioo' erwärmte Lösung von Sulfo- salicy1säure, z. B. eine iLösung von 15 kg Sulfo- salicylsäure in 35 kg U'as@ser, die entsprechende Menge von p-Aminobenzolsulfonaniid oder eines Derivats dieser Verbindung, z. B. p-Amino- benzolsulfonami.dothiazol oder p-Aminobenzol- acetsulfonamid oder 1i-_Aininobenzolsulfon- amidopyridin bei einer Temperatur von etwa 23o bis ioo', vorzugsweise 9o bis 95', einge- tragen wird und die gebildete Verbindung durch Abkühlenlassen der Lösung zur Ausscheidung gebracht wird.
PATENT APPLICATION: i. Process for the production of sulfo- salicylates of p-Aniinobenzolsulfonaini @ ds and its derivatives through the interaction of the Components in aqueous solution, @due to this indicates that the unisposition in concentrated trated solution in the heat, e.g. B. at about 8o to 100 ', preferably 9o to 95', performed men will. 2. The method according to claim i, characterized in that indicates that in a focused, on about 8o to ioo 'heated solution of sulfo- salicic acid, e.g. B. a solution of 15 kg sulfo- salicylic acid in 35 kg U'as @ ser, the corresponding Amount of p-aminobenzenesulfonaniide or one Derivative of this compound, e.g. B. p-amino benzenesulfonami.dothiazole or p-aminobenzene- Acetsulfonamid or 1i-_Aininobenzolsulfon- amidopyridine at a temperature of about 23o to 100 ', preferably 9o to 95', will carry and the connection formed through Allow the solution to cool for excretion is brought.
DEP6600D 1948-04-23 1948-10-02 Process for the preparation of sulfosalicylates of p-aminobenzenesulfonamide Expired DE833041C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR833041X 1948-04-23

Publications (1)

Publication Number Publication Date
DE833041C true DE833041C (en) 1952-03-03

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ID=9296343

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DEP6600D Expired DE833041C (en) 1948-04-23 1948-10-02 Process for the preparation of sulfosalicylates of p-aminobenzenesulfonamide

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