CH185343A - Process for the preparation of a sulfenamide. - Google Patents

Process for the preparation of a sulfenamide.

Info

Publication number
CH185343A
CH185343A CH185343DA CH185343A CH 185343 A CH185343 A CH 185343A CH 185343D A CH185343D A CH 185343DA CH 185343 A CH185343 A CH 185343A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
sulfenamide
hexahydroethylaniline
benzene
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 CH185343A publication Critical patent/CH185343A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/76—Sulfur atoms attached to a second hetero atom
    • C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom

Description

  

      Verfahren    zur Herstellung eines Sulfonamids.    Gegenstand vorliegender Erfindung ist  die     Herstellung    eines Sulfonamids durch       Pehandlung    von     2-Merkaptobenzothiazol    und       Hexahydroäthylanilin    mit     Natriumhypo-          chlorit.    Die Umsetzung     wird    in     wässrigem          1ledium    mit oder ohne Zusatz     indifferenter     organischer     Lösungsmittel    durchgeführt.

   Sie  geht schon bei niedriger Temperatur vor sich,  kann aber durch     Erwärmen        beschleunigt     werden.  



  Das nach diesem Verfahren erhältliche  bereits bekannte Sulfonamid kann als Hilfs  stoff in der     Kautschukindustrie    Verwendung  finden.  



       Beispiel:     50 kg     2-;VIercaptobenzothiazol,    mit<B>300</B>  Liter Wasser     verrührt,    werden mit 114 kg       Hexahydroäthylanilin    versetzt und durch Er  wärmen auf 50   in Lösung gebracht. Nach  Rückkühlen auf 35   läuft eine     wässrige    Lö  sung von 21,6 kg     Natriumhypochlorit    inner  halb 6 Stunden zu.

   Nach     einstündigem            Nachrühren    wird mit     etwa    300 Liter Wasser  verdünnt.     Die        wässrige    Lösung     wird    von den  öligen Anteilen abgetrennt.     Letztere    werden  in Benzol aufgenommen, worauf die     ben-          zolische    Lösung zwecks Befreiung vom     Übei-          schiissio;    angewandten     Hexahydroäthylanilin     mit sehr verdünnter Salzsäure kalt verrührt  und dann neutral gewaschen wird.

   Nach       Abdestillieren    des Benzols unter verminder  tem Druck     hinterbleibt    das     Benzothiazolyl-          2-sulfenhexahydroäthylanilid:     
EMI0001.0038     
    als dickes 01 in einer Menge von 67 kg,  entsprechend     75,5%    der     Theorie.  



      Process for the preparation of a sulfonamide. The present invention relates to the preparation of a sulfonamide by treating 2-mercaptobenzothiazole and hexahydroethylaniline with sodium hypochlorite. The reaction is carried out in aqueous 1ledium with or without the addition of inert organic solvents.

   It already takes place at a low temperature, but it can be accelerated by heating.



  The already known sulfonamide obtainable by this process can be used as an auxiliary material in the rubber industry.



       Example: 50 kg of 2-; VIercaptobenzothiazole, stirred with <B> 300 </B> liters of water, are mixed with 114 kg of hexahydroethylaniline and brought into solution by heating to 50. After cooling back to 35, an aqueous solution of 21.6 kg of sodium hypochlorite runs in within 6 hours.

   After stirring for one hour, the mixture is diluted with about 300 liters of water. The aqueous solution is separated from the oily components. The latter are taken up in benzene, whereupon the benzene solution for the purpose of liberation from the ubichiissio; applied hexahydroethylaniline is stirred cold with very dilute hydrochloric acid and then washed neutral.

   After the benzene has been distilled off under reduced pressure, the benzothiazolyl-2-sulfenhexahydroethylanilide remains:
EMI0001.0038
    as thick 01 in an amount of 67 kg, corresponding to 75.5% of theory.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Sulfon amids, dadurch gekennzeichnet, dass man EMI0002.0001 2-11lerkaptobenzothiazol <SEP> und <SEP> Idexahydroäthyl anilin <SEP> in <SEP> wässrigem <SEP> Medium <SEP> mit <SEP> Natrium 11y <SEP> poelilorit <SEP> behandelt. EMI0002.0002 ÜNTEUANSPRUCEt <tb> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gehennzeichnet,' <SEP> dass <SEP> ein <SEP> indifferentes <SEP> orga nisehes <SEP> Lösungsmittel <SEP> zugesetzt <SEP> wird. PATENT CLAIM: Process for the production of a sulfon amide, characterized in that one EMI0002.0001 2-11lerkaptobenzothiazol <SEP> and <SEP> idexahydroethyl aniline <SEP> in <SEP> aqueous <SEP> medium <SEP> treated with <SEP> sodium 11y <SEP> poelilorit <SEP>. EMI0002.0002 UNTEUPRUCEt <tb> Method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> is marked, '<SEP> that <SEP> an <SEP> inert <SEP> organic <SEP> solvent <SEP> is added to <SEP>.
CH185343D 1935-02-14 1935-02-14 Process for the preparation of a sulfenamide. CH185343A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH182394T 1935-02-14
CH185343T 1935-02-14

Publications (1)

Publication Number Publication Date
CH185343A true CH185343A (en) 1936-07-15

Family

ID=25720701

Family Applications (1)

Application Number Title Priority Date Filing Date
CH185343D CH185343A (en) 1935-02-14 1935-02-14 Process for the preparation of a sulfenamide.

Country Status (1)

Country Link
CH (1) CH185343A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762814A (en) * 1953-11-27 1956-09-11 Monsanto Chemicals Production of vulcanization accelerators

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2762814A (en) * 1953-11-27 1956-09-11 Monsanto Chemicals Production of vulcanization accelerators

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