CH209121A - Process for preparing a sulfonic acid amide compound. - Google Patents

Process for preparing a sulfonic acid amide compound.

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Publication number
CH209121A
CH209121A CH209121DA CH209121A CH 209121 A CH209121 A CH 209121A CH 209121D A CH209121D A CH 209121DA CH 209121 A CH209121 A CH 209121A
Authority
CH
Switzerland
Prior art keywords
sulfonic acid
methylbenzene
amide compound
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 CH209121A publication Critical patent/CH209121A/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

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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.       Das Hauptpatent betrifft ein Verfahren  zur Darstellung einer therapeutisch wertvollen       Sulfonsäureamidverbindung.    Gegenstand des  vorliegenden Patentes ist ein Verfahren zur  Herstellung einer     Sulfonsäureamidverbindung,     dadurch gekennzeichnet, dass man     1-Acyl-          amino-2-methoxy-5-methylbenzol    durch Ein  wirken von     Chlorsulfonsäure    in     1-Acylamino-2-          methoxy-5-methylbenzol-4-sulfonsäurechlorid     überführt,

   diese Verbindung durch Einwirken  von     Konoinethylamin    in 1-Acylamino-2       methoxy-5-inethylbenzol-4-sulfonsäuremono-          methylamid    überführt und aus dieser 'Ver  bindung die     Acylgruppe    durch     Verseifung     abspaltet.  



  Das so erhältliche     1-Amino-2-methoxy-5-          methylbenzol-    4 -     sulfonsäuremonomethylamid     bildet farblose Kristalle vom Schmelzpunkt  139 0. Es soll therapeutische Anwendung  finden.  



  <I>Beispiel:</I>  100 g     1-Acetylamino-2-methoxy-5-methyl-          benzol    (aus Benzol weisse Kristalle vom    Schmelzpunkt 1120) werden bei 20 0 in  300 cm'     Chlorsulfonsäure    eingetragen. Die       Mischung    wird anschliessend 4 Stunden auf  70 0 erhitzt. Sodann wird in Eiswasser ein  gerührt und das ausgefällte     1-Acetylamino-2-          methoxy-5-methylbenzol-4-sulfousäurechlorid     abgesaugt. Es bildet nach dem     Umkristalli-          sieren    aus     wässrigem    Aceton farblose Kristalle  vom Schmelzpunkt 135 0.

   Zur Überführung  in das     Monomethyla.mid    wird das von über  schüssiger Mineralsäure durch 'Auswaschen  befreite, noch feuchte Chlorid in 400 cm-'  Wasser und mindestens 2     Mol        Monomethyl-          amin        angeschlämmt    und 30 Minuten bei 60  bis 70 0 gerührt.

   Nach dem Abkühlen wird  das     1-Acetylamino-2-methoxy.5.methylbenzol-          4-sulfonsäuremonomethylamid    abgesaugt und  durch     Umlösen    aus Natronlauge und Am  moniumchlorid gereinigt. 50 g dieser     Ver-          bindung        werden        mit        250        cm3        20        %iger        Natron-          lauge    unter Rühren gekocht.

   Aus der Mi  schung wird das entstandene     1-Amino-2-          methoxy-    5     -methylb        enzol-4-        sulfonsäuremon    o-           methylamid    nach dem Erkalten durch Ab  stumpfen des Alkalis mit Essigsäure oder       Ammoniumchlorid    ausgefällt. Es bildet nach  dem     Umkristallisieren    aus verdünntem Alko  hol farblose Kristalle vorn     Schmelzpunkt    139 .



  Process for preparing a sulfonic acid amide compound. The main patent relates to a process for the preparation of a therapeutically useful sulfonic acid amide compound. The subject of the present patent is a process for the preparation of a sulfonic acid amide compound, characterized in that 1-acyl-amino-2-methoxy-5-methylbenzene by an action of chlorosulfonic acid in 1-acylamino-2-methoxy-5-methylbenzene-4- sulfonic acid chloride transferred,

   this compound is converted into 1-acylamino-2-methoxy-5-ynethylbenzene-4-sulfonic acid monomethylamide by the action of konoinethylamine and the acyl group is split off from this compound by saponification.



  The 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid monomethylamide obtainable in this way forms colorless crystals with a melting point of 139 0. It is said to be of therapeutic use.



  <I> Example: </I> 100 g of 1-acetylamino-2-methoxy-5-methylbenzene (white crystals from benzene with a melting point of 1120) are introduced into 300 cm of chlorosulfonic acid at 20 °. The mixture is then heated to 70 ° for 4 hours. It is then stirred into ice water and the 1-acetylamino-2-methoxy-5-methylbenzene-4-sulfous acid chloride which has precipitated is filtered off with suction. After recrystallization from aqueous acetone, it forms colorless crystals with a melting point of 135 °.

   To convert the excess mineral acid into the Monomethyla.mid, the still moist chloride, freed from excess mineral acid, is suspended in 400 cm- 'of water and at least 2 mol of monomethylamine and stirred at 60 to 70 ° for 30 minutes.

   After cooling, the 1-acetylamino-2-methoxy.5.methylbenzene-4-sulfonic acid monomethylamide is filtered off with suction and purified by dissolving it from sodium hydroxide solution and ammonium chloride. 50 g of this compound are boiled with 250 cm3 of 20% sodium hydroxide solution while stirring.

   The resulting 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid mono-methylamide is precipitated from the mixture after cooling by blunting the alkali with acetic acid or ammonium chloride. After recrystallization from dilute alcohol, it forms colorless crystals with a melting point of 139.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung einer Sulfon- säureamidverhindung, dadurch gekennzeich net, dass man 1-Acylarnirio.2.methoxy.5-niethyl- benzol durch Einwirken von Chlorsulfonsäure in 1-Acylamirio-2-metlioxy-5-methylbenzol-4- sulfonsäurechlorid überführt, <B> PATENT CLAIM: </B> Process for the preparation of a sulfonic acid amide compound, characterized in that 1-acylamine.2.methoxy.5-niethylbenzene is converted into 1-acylamine-2-metlioxy-5 by the action of chlorosulfonic acid -methylbenzene-4-sulfonic acid chloride transferred, diese Verbindung durch Einwirken von Monomethylamin in 1-Acylarnino-2-metboxy -5-metliylbenzol-4-sul- fonsäurernotiornethylamid überführt und aus dieser Verbindung die Acylgruppe durch Ver- seifung abspaltet. Das so erhältliche 1-Amirio-2-metboxy-5- methylbenzol - 4 - "ulforrsäurenionomethylamid bildet farblose Kristalle vorn Schmelzpunkt 139 . this compound is converted into 1-acylamino-2-metboxy -5-methylbenzene-4-sulphonic acid non-methylamide by the action of monomethylamine and the acyl group is split off from this compound by saponification. The 1-amirio-2-metboxy-5-methylbenzene-4- "ulforrsäurionomethylamid thus obtainable forms colorless crystals with a melting point of 139.
CH209121D 1937-03-04 1938-02-22 Process for preparing a sulfonic acid amide compound. CH209121A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE209121X 1937-03-04
CH203550T 1938-02-22

Publications (1)

Publication Number Publication Date
CH209121A true CH209121A (en) 1940-03-15

Family

ID=25723944

Family Applications (1)

Application Number Title Priority Date Filing Date
CH209121D CH209121A (en) 1937-03-04 1938-02-22 Process for preparing a sulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH209121A (en)

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