CH240726A - Process for the preparation of a p-amino-benzenesulfonamide. - Google Patents

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

Info

Publication number
CH240726A
CH240726A CH240726DA CH240726A CH 240726 A CH240726 A CH 240726A CH 240726D A CH240726D A CH 240726DA CH 240726 A CH240726 A CH 240726A
Authority
CH
Switzerland
Prior art keywords
amino
preparation
dimethyl
benzenesulfonamide
nitro
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 CH240726A publication Critical patent/CH240726A/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 -     N,    -     (ss,ss-dimethyl-          acroyl)-sulfonamides,    welches dadurch ge  kennzeichnet ist, dass man ein     4-Nitro-benzol-          sulfonsäurehalogenid    mit einem Salz des       ss,ss-Dimethyl-acrylsäureamids    umsetzt und  im entstandenen 4 -     Nitro    -Benzol - N -     (ss,ss-di-          methylacroyl)

  -sulfonamid    die Nitrogruppe  zur     Aminogruppe    reduziert.    <I>Beispiel:</I>    10 Teile     ss,ss-Dimethyl-acrylsäureamid    wer  den in 200 Teilen absolutem     Toluol    gelöst,  mit 4 Teilen     Natriumamid    versetzt und durch       .'/2stündiges    Sieden ins     Natriumsalz    überge  führt.

   Nach dem Erkalten lässt man eine Lö  sung von 22 Teilen     p-Nitro-benzolsulfochlo-          rid    in<B>100</B> Teilen absolutem     Toluol    zufliessen    und erhitzt 2 Stunden unter Rühren und       Rückfluss:    Das     Toluol    wird im Vakuum ab  destilliert, der Rückstand in Soda gelöst, die  Lösung filtriert und angesäuert.

   Man erhält,  aus Alkohol umkristallisiert, das     4-Nitro-          benzol    - N -     (ss,ss    -     dimethyl    -     acroyl)-sulfonamid     vom Schmelzpunkt 155 , und daraus durch  Reduktion die entsprechende     Aminoverbin-          dung.  



  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 - N, - (ss, ss-dimethyl-acroyl) -sulfonamides, which is characterized in that a 4-nitro-benzenesulfonic acid halide with a Reacts salt of ss, ss-dimethyl-acrylamide and in the resulting 4 - nitro-benzene - N - (ss, ss-dimethyl acrylate)

  -sulfonamide reduces the nitro group to the amino group. <I> Example: </I> 10 parts of ss, ss-dimethyl-acrylic acid amide are dissolved in 200 parts of absolute toluene, mixed with 4 parts of sodium amide and converted into the sodium salt by boiling for 1/2 hour.

   After cooling, a solution of 22 parts of p-nitrobenzenesulfochloride in 100 parts of absolute toluene is allowed to flow in and the mixture is heated for 2 hours with stirring and reflux: the toluene is distilled off in vacuo, the residue dissolved in soda, the solution filtered and acidified.

   Recrystallized from alcohol, 4-nitrobenzene-N- (ss, ss-dimethyl-acroyl) -sulfonamide with a melting point of 155 is obtained, and the corresponding amino compound is obtained therefrom by reduction.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des bekannten 4-Amino-benzol-Nl-(ss,ss-dimethyl-acroyl)-sul- fonamides, dadurch gekennzeichnet, dass man ein 4-Nitro-benzolsulfonsäurehalogenid mit einem Salz des ss,ss-Dimethyl-aerylsäureamids umsetzt und im entstandenen 4-Nitro-benzol- N-(ss,ss-dimethyl-acroyl)-sifjflinamid die Ni- trogruppe zur Aminogruppe-reduziert. PATENT CLAIM: Process for the preparation of the known 4-amino-benzene-Nl- (ss, ss-dimethyl-acroyl) -sulphonamides, characterized in that a 4-nitro-benzenesulphonic acid halide is mixed with a salt of ss, ss-dimethyl aerylsäureamids and in the resulting 4-nitro-benzene-N- (ss, ss-dimethyl-acroyl) -sifjflinamid-reduced the nitro group to the amino group.
CH240726D 1943-04-09 1943-04-09 Process for the preparation of a p-amino-benzenesulfonamide. CH240726A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH240726T 1943-04-09
CH237880T 1943-05-14

Publications (1)

Publication Number Publication Date
CH240726A true CH240726A (en) 1946-01-15

Family

ID=25728283

Family Applications (1)

Application Number Title Priority Date Filing Date
CH240726D CH240726A (en) 1943-04-09 1943-04-09 Process for the preparation of a p-amino-benzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH240726A (en)

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