CH242291A - Process for the preparation of a p-amino-benzenesulfonamide. - Google Patents

Process for the preparation of a p-amino-benzenesulfonamide.

Info

Publication number
CH242291A
CH242291A CH242291DA CH242291A CH 242291 A CH242291 A CH 242291A CH 242291D A CH242291D A CH 242291DA CH 242291 A CH242291 A CH 242291A
Authority
CH
Switzerland
Prior art keywords
amino
preparation
benzenesulfonamide
dimethylbenzoyl
acylamino
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH242291A publication Critical patent/CH242291A/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 Herstellung eines     p-Amino-benzolsulfonamides.       Gegenstand vorliegenden Zusatzpatentes  ist ein     Verfahren    zur Herstellung des be  kannten     4-Amino-benzol-N1-(3',4'-dimethyl-          benzoyl)-sülfonamides,    welches dadurch ge  kennzeichnet ist, dass man ein     4-Aoylamino-          benzolsulfonsäurehalogenid    mit einem Salz  des     3,4-Dimethylbenzamides    umsetzt und im       entstandenen        4-Acylamino-benzol-N,-(3',4'-          dimethylbenzoyl)

  -sulfonamid    die     Acylamino-          gruppe    zur freien     Aminogruppe    verseift.  



  <I>Beispiel:</I>  15 Teile     3,4-Dimethylbenzamid    werden  in 200 Teilen absolutem     Toluol    gelöst. Man  gibt 2,3 Teile     Natrium    zu     und    erwärmt unter  Rühren und     Rückfluss    bis zum Verschwinden  des Natriums. Nach dem     Erkalten    lässt man  eine Lösung von     N-Carbäthogy-sulfanilsäure-          chlorid    in absolutem     Toluol    zufliessen und er  wärmt anschliessend 2-     Stunden    zum Sieden.

    Das     Toluol    wird im Vakuum     abdestilliert,       der Rückstand in verdünnter Natronlauge  gelöst, mit Tierkohle geklärt und filtriert.  Aus dem Filtrat erhält man durch An  säuern und Kristallisation des ausgefallenen  Produktes aus Alkohol das     N4        Carbäthogy-          aminobenzol    -     N1-        (3',4'-dimethylbenzoyl)    -     sul-          fonamid    vom     Schmelzpunkt    255 ;

   daraus       wird    durch     Verseifi-mg    das freie     Aminoderi-          vat    hergestellt.



  Process for the preparation of a p-amino-benzenesulfonamide. The present additional patent is a process for the preparation of the known 4-amino-benzene-N1- (3 ', 4'-dimethyl-benzoyl) -sulfonamide, which is characterized in that a 4-aoylamino-benzenesulfonic acid halide is used with a salt of the 3,4-dimethylbenzamide and in the resulting 4-acylamino-benzene-N, - (3 ', 4'-dimethylbenzoyl)

  sulfonamide saponifies the acylamino group to form a free amino group.



  <I> Example: </I> 15 parts of 3,4-dimethylbenzamide are dissolved in 200 parts of absolute toluene. 2.3 parts of sodium are added and the mixture is heated with stirring and reflux until the sodium disappears. After cooling, a solution of N-carbethogy-sulfanilic acid chloride in absolute toluene is allowed to flow in and it is then warmed to the boil for 2 hours.

    The toluene is distilled off in vacuo, the residue is dissolved in dilute sodium hydroxide solution, clarified with animal charcoal and filtered. By acidifying the filtrate and crystallizing the precipitated product from alcohol, N4 carbethogyaminobenzene - N1- (3 ', 4'-dimethylbenzoyl) - sulfonamide with a melting point of 255;

   the free amino derivative is produced from this by saponification.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des bekannten 4-Amino-benzol-N,-(3',4'-dimethylbenzoyl)- sulfonamides, dadurch Gekennzeichnet, dass man ein 4 - Acylamino - benzolsulfonsäure- halogenid mit einem Salz des 3,4-Dimethyl- benzamides umsetzt und im entstandenen 4- Acyl - aminobenzol - N1 - (3', 4' - dimethylben- zoyl) PATENT CLAIM: Process for the preparation of the known 4-amino-benzene-N, - (3 ', 4'-dimethylbenzoyl) - sulfonamides, characterized in that a 4 - acylamino - benzenesulfonic acid halide with a salt of 3,4-dimethyl - converts benzamides and in the resulting 4-acyl - aminobenzene - N1 - (3 ', 4' - dimethylbenzoyl) -sulfonamid die Acylaminogruppe zur freien Aminogruppe verseift. -sulfonamide saponifies the acylamino group to the free amino group.
CH242291D 1943-05-14 1943-05-14 Process for the preparation of a p-amino-benzenesulfonamide. CH242291A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242291T 1943-05-14
CH237880T 1943-05-14

Publications (1)

Publication Number Publication Date
CH242291A true CH242291A (en) 1946-04-30

Family

ID=25728285

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242291D CH242291A (en) 1943-05-14 1943-05-14 Process for the preparation of a p-amino-benzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH242291A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6235680B1 (en) 1996-05-29 2001-05-22 Hoechst Schering Agrevo Gmbh N-acylsulfonamides, novel mixtures of herbicides and antidotes, and their use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6235680B1 (en) 1996-05-29 2001-05-22 Hoechst Schering Agrevo Gmbh N-acylsulfonamides, novel mixtures of herbicides and antidotes, and their use

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