CH193224A - Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure. - Google Patents

Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure.

Info

Publication number
CH193224A
CH193224A CH193224DA CH193224A CH 193224 A CH193224 A CH 193224A CH 193224D A CH193224D A CH 193224DA CH 193224 A CH193224 A CH 193224A
Authority
CH
Switzerland
Prior art keywords
alkylindole
acid
sodium salt
sulfonic acid
toluidide
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH193224A publication Critical patent/CH193224A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

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

Description

  

  Verfahren     zur    Herstellung des     Natriumsalzes    der     Sulfonsäure    des     a-Alkylindols,     das aus dem     o-Tolnidid    der     Campholsäure    durch     Ringschluss        herstellbar    ist.

      Es wurde gefunden, dass man zu einer  neuen, wertvollen     Verbindung,    dem Natrium  salz der     Sulfonsäure    des     a-Alkylindols,    das  aus dem     o-Toluidid    der     Campholsäure    durch       Ringschluss    darstellbar     ist,    gelangt, wenn  man dieses     a-Alkylindol    unter     milden    Be  dingungen so lange mit     sulfonierenden    Mit  teln behandelt, bis Wasserlöslichkeit erreicht  ist,

   und durch Neutralisieren mit Natron  lauge die durch     Ausgiessen    in Eiswasser ab  geschiedene     Sulfonsäure    in das     Natriumsalz     überführt. Dieses wird als     weisses    Pulver er  halten, das in wässriger Lösung gute     kapil-          laraktive    Eigenschaften aufweist.

   Es soll       insbesondere    als Netz-,     Dispergier-,        Emul-          gier-.        Durchdringungs-    und     Waschmittel,     insbesondere als     galkseifenemulgator,    die  nen; es kann aber auch     Verwendung    finden  als Mittel zum Weichmachen und Appretie  ren.

   Das als Ausgangsmaterial     dienende          a-Alkylindol    kann aus dem     o-Toluidid    der       Campholsäure    durch     Ringschluss    mit Na  triumalkoholat nach     Madelung    (Bor. 45, Seite    1128), oder mit     Natriumamid    nach     Verley          (Bul.    de la     Soc.        Chim.    1924, S. 1039/40 und  1925, S.     189/91)    dargestellt werden.  



  <I>Beispiel:</I>       In    ein Gemisch von 30 Teilen Monohydrat  und 30 Teilen     Oleum    26%ig werden bei  <B>10'</B> C 15 Teile des     a-Alkylindols    aus     Cam-          pholsäure-o-toluidid    eingetragen und 14 Stun  den bei dieser     Temperatur    gerührt. Nachdem  eine Probe die Wasserlöslichkeit beim Neu  tralisieren ergibt, wird die     Reaktionsmasse     auf Eis gegossen, die ausgeschiedene     Sulfon-          säure    abgetrennt und neutralisiert. Man er  hält nach dem Eindampfen ein weisses Pul  ver, das in wässriger Lösung gute kapillar  aktive Eigenschaften aufweist.



  Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-tolnidide of campholic acid by ring closure.

      It has been found that a new, valuable compound, the sodium salt of the sulfonic acid of a-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure, can be obtained if this a-alkylindole is kept under mild conditions for so long treated with sulfonating agents until solubility in water is achieved,

   and by neutralizing with sodium hydroxide solution, the sulfonic acid which has separated out by pouring into ice water is converted into the sodium salt. This is obtained as a white powder which has good capillary-active properties in an aqueous solution.

   It should be used in particular as a wetting, dispersing, emulsifying. Penetrants and detergents, in particular as a gall soap emulsifier, the NEN; But it can also be used as a softening and finishing agent.

   The a-alkylindole serving as starting material can be obtained from the o-toluidide of campholic acid by ring closure with sodium alcoholate according to Madelung (Bor. 45, page 1128), or with sodium amide according to Verley (Bul. De la Soc. Chim. 1924, p. 1039 / 40 and 1925, pp. 189/91).



  <I> Example: </I> In a mixture of 30 parts of monohydrate and 30 parts of 26% oleum at <B> 10 '</B> C, 15 parts of the α-alkylindole from campholic acid o-toluidide are introduced and stirred for 14 hours at this temperature. After a sample shows the water solubility on neutralization, the reaction mass is poured onto ice, the sulphonic acid which has separated out is separated off and neutralized. After evaporation, it is a white powder that has good capillary-active properties in an aqueous solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des Natrium salzes der Sulfonsäure des a-Alkylindols, das aus Campholsäur e-o-toluidid durch Ring schluss darstellbar ist, dadurch gekennzeich- net, dass man dieses a-Alkylindol unter mil den Bedingungen so lange mit sulfonierenden Mitteln behandelt, bis Wasserlöslichkeit er reicht ist, PATENT CLAIM: Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from campholic acid eo-toluidide by ring closure, characterized in that this α-alkylindole is treated with sulfonating agents under mild conditions until Water solubility is reached, und dass man durch Neutralisieren die durch Ausgiessen in Eiswasser abgeschie dene Sulfonsäure in das Natriumsalz über führt. Dieses wird als weisses Pulver erhal ten, das in wässriger Lösung gute kapillar- aktive Eigenschaften aufweist. and that the sulfonic acid deposited by pouring into ice water is converted into the sodium salt by neutralization. This is obtained as a white powder that has good capillary-active properties in an aqueous solution. Es soll ins besondere als Netz-, Dispergier-, Emulgier-, Durchdringungs- und Waschmittel, insbeson dere als galkseifenemulgator dienen; es kann aber auch Verwendung finden als Mittel zum Weichmachen und Appretieren. It should serve in particular as a wetting, dispersing, emulsifying, penetrating and detergent, in particular as a galkseifenemulsgator; but it can also be used as a softening and finishing agent.
CH193224D 1936-05-14 1936-05-14 Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure. CH193224A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH191011T 1936-05-14
CH193224T 1936-05-14

Publications (1)

Publication Number Publication Date
CH193224A true CH193224A (en) 1937-09-30

Family

ID=25722071

Family Applications (1)

Application Number Title Priority Date Filing Date
CH193224D CH193224A (en) 1936-05-14 1936-05-14 Process for the preparation of the sodium salt of the sulfonic acid of α-alkylindole, which can be prepared from the o-toluidide of campholic acid by ring closure.

Country Status (1)

Country Link
CH (1) CH193224A (en)

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