CH201207A - Process for preparing a sulfonic acid amide compound. - Google Patents

Process for preparing a sulfonic acid amide compound.

Info

Publication number
CH201207A
CH201207A CH201207DA CH201207A CH 201207 A CH201207 A CH 201207A CH 201207D A CH201207D A CH 201207DA CH 201207 A CH201207 A CH 201207A
Authority
CH
Switzerland
Prior art keywords
acid
sulfonic acid
amide compound
acid amide
preparing
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 CH201207A publication Critical patent/CH201207A/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 Darstellung einer     Sulfonsäureamidverbindung.       Es wurde gefunden, dass die     Acylamino-          benzolsulfonsäureamide,    deren     Acylrest    min  destens 5     Kohlenstoffatome    enthält, thera  peutisch, im besonderen gegen     Streptokokken-          infektionen    gut wirksame Produkte dar  stellen.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer     Sulfon-          säureamidverbindung,    welches dadurch ge  kennzeichnet ist, dass man eine Verbindung,  welche sich von der Ölsäure dadurch unter  scheidet, dass sie an Stelle der     OH-Gruppe     einen reaktionsfähigeren Rest besitzt, auf     4-          Aminobenzolsulfonsäure-methylamid    einwir  ken lässt. Als reaktionsfähigen Abkömmling  der Ölsäure kann man deren     Halogenide,    vor  zugsweise das     Ülsäurechlorid,    oder ihr     Anhy-          drid    oder ihre Ester verwenden.

   Bei Verwen  dung der     Halogenide    arbeitet man zweck  mässig in Gegenwart eines säurebindenden  Mittels, beispielsweise     Pyridin.    Das Reak  tionsprodukt wird zweckmässig durch Behan-         deln    mit verdünnter Säure aus der Reaktions  mischung abgeschieden. Nach dem     Tim-          kristallisieren,    z. B. aus Methanol, erhält man  das 4 -     Oleylaminobenzolsulfonsäuremethyl-          amid    in Kristallen vom     Schmelzpunkt    105  .  Es ist in Wasser und     verdünnter    Säure nicht  löslich und soll therapeutische Anwendung  finden.  



  <I>Beispiel:</I>  18,6 g     4-Aminobenzolsulfonsäuremethyl-          amid    werden in 50 cm'     Pyridin    mit 30 g       Ölsäurechlorid    30 Minuten im Wasserbade  erhitzt. Nach Eingiessen     in    kalte verdünnte  Salzsäure wird der allmählich erstarrende  Niederschlag abgesaugt und aus wenig Me  thanol umkristallisiert. Man erhält das     4-          Oleylaminobenzolsulfonsäuxemethylamid    als  fettige Kristallmasse vom Schmelzpunkt<B>105'.</B>



  Process for preparing a sulfonic acid amide compound. It has been found that the acylaminobenzenesulphonic acid amides, the acyl radical of which contains at least 5 carbon atoms, are therapeutically effective, in particular products that are effective against streptococcal infections.



  The subject of the present patent is a process for the production of a sulfonic acid amide compound, which is characterized in that a compound which differs from oleic acid in that it has a more reactive radical instead of the OH group is converted to 4- Aminobenzenesulfonic acid methylamide can act. Its halides, preferably oleic acid chloride, or its anhydride or its esters can be used as the reactive derivative of oleic acid.

   When using the halides one works expediently in the presence of an acid-binding agent, for example pyridine. The reaction product is expediently separated from the reaction mixture by treatment with dilute acid. After Tim crystallization, e.g. B. from methanol, the 4 - oleylaminobenzene sulfonic acid methyl amide is obtained in crystals with a melting point of 105. It is not soluble in water and dilute acid and is intended to be used therapeutically.



  <I> Example: </I> 18.6 g of 4-aminobenzenesulfonic acid methylamide are heated in a 50 cm pyridine with 30 g of oleic acid chloride for 30 minutes in a water bath. After pouring into cold, dilute hydrochloric acid, the gradually solidifying precipitate is filtered off with suction and recrystallized from a little methanol. The 4-oleylaminobenzene sulfonic acid methylamide is obtained as a fatty crystalline mass with a melting point of <B> 105 '. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Sulfon- säureamidverbindung, dadurch gekennzeich- net, dass man eine Verbindung, die sich von der Ölsäure dadurch unterscheidet, dass sie an Stelle der OH-Gruppe einen reaktions fähigeren Rest besitzt, auf 4 Aniinobenzol- siilfotisäuremethylamid einwirken lässt. PATENT CLAIM: Process for the production of a sulfonic acid amide compound, characterized in that a compound which differs from oleic acid in that it has a more reactive radical instead of the OH group is allowed to act on 4 aniinobenzenesilfotic acid methylamide. Das so erhältliche 4-Oleylaminobenzolsul- fonsäuremethylamid bildet Kristalle vom Schmelzpunkt 105 und ist in Wasser und verdünnter Säure unlöslich. UNTERANSPRüCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet. dass man ein Ölsäure- ha.lo"enid verwendet und in CTegenwat-t eines säurebindenden Mittels arbeitet. 2. The 4-oleylaminobenzenesulfonic acid methylamide obtainable in this way forms crystals with a melting point of 105 and is insoluble in water and dilute acid. SUBClaims: 1. Method according to claim, characterized. that one uses an oleic acid ha.lo "enide and works in CTegenwat-t of an acid-binding agent. 2. Verfahren nach Patentanspruch Lind Un- teranspruch 1, dadurch gekennzeichnet. dass man als säurebindendes _lfittel ]\vri- din verwendet. Method according to patent claim and sub-claim 1, characterized. that \ vridin is used as an acid-binding solvent.
CH201207D 1936-04-18 1937-04-03 Process for preparing a sulfonic acid amide compound. CH201207A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE201207X 1936-04-18
CH197427T 1937-04-03

Publications (1)

Publication Number Publication Date
CH201207A true CH201207A (en) 1938-11-15

Family

ID=25722986

Family Applications (1)

Application Number Title Priority Date Filing Date
CH201207D CH201207A (en) 1936-04-18 1937-04-03 Process for preparing a sulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH201207A (en)

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