CH242518A - Process for the preparation of an acylated sulfonamide. - Google Patents

Process for the preparation of an acylated sulfonamide.

Info

Publication number
CH242518A
CH242518A CH242518DA CH242518A CH 242518 A CH242518 A CH 242518A CH 242518D A CH242518D A CH 242518DA CH 242518 A CH242518 A CH 242518A
Authority
CH
Switzerland
Prior art keywords
amino
dimethyl
sulfonamide
acroyl
benzene
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 CH242518A publication Critical patent/CH242518A/en

Links

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
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     aeylierten    Sulfonamides.-    <B>-_</B> vorliegenden Patentes ist ein  Verfahren zur     Herstellung    des bekannten  4. -     Amino-benzol    -     N1-        (ss,ss-dimetliyl    -     acroyl)-          sulfonamids.    Das Verfahren ist dadurch ge  kennzeichnet,     daB    man ein substituiertes       4-Amino-benzolsulfonamid    der Formel  
EMI0001.0010     
    in der R     einen    durch     hydrolysierende        Mittel          abspaltbaren    Rest bedeutet,

   durch     Verseifung          in        4-Amino-benzol-N,-(ss,ss-dimethyl-acroyl)-          sulfonamid    überführt.  



  Die     Verbindung        bildet-farblose,    Kristalle  vom     Schmelzpunkt        184-185 .    Sie soll als  Arzneimittel     Verwendung        finden.     



  <I>Beispiel 1:</I>  10     Teile        N-(4-Amino-benzolsulfonyl)-          ss,ss-dimethyl-acrylamidin    vom Schmelzpunkt  128-129  und der Formel  
EMI0001.0028     
    werden mit 100 Teilen 3,5 %     iger    Salzsäure  2     Stunden    auf 90-100  erhitzt. Nach dem  Erkalten wird     sodaalkalisch    gestellt, filtriert  und mit Essigsäure angesäuert. Man- erhält  das     4-Amino-benzol-N,-(ss,ss-dimethyl-acroyl)-          sulfonamid.    Aus Alkohol umkristallisiert  bildet es farblose Kristalle vom Schmelz=       punkt        184-185 .     



  <I>Beispiel 2:</I>  10 Teile     N-(4-Amino-benzolsulfonyl)-ss,ss-          dimethyl-acryliminoäthyläther    vom     Schmelz-          Punkt    116      und    der Formel  
EMI0001.0041     
         werden,    mit 200 Teilen 2     %iger    Salzsäure  2     Stunden    auf 90-100  erhitzt. Nach dem           Erkälten        wird        sodaalkalisch    gestellt,     filtriemt          und    mit Essigsäure angesäuert.

   Man erhält  das     4-Amino-benzol-Nl-(ss,ss-dimethyl-acroyl)-          sulfonamid.        Aus    Alkohol     umkristallisiert     bildet es farblose     Kristalle    vom Schmelz  punkt 184-185 .  



  <I>Beispiel 3;</I>  10 Teile     N-(4-Amino-benzolsulfo@nyl)-N'-          äthyl-ss,ss-dimethyl-aerylamidin    vom Schmelz  punkt 220-222  der Formel  
EMI0002.0013     
    werden mit 200     Teilen    3,5     %iger    Salzsäure  31/2     Stunden    auf 90-100  erhitzt. Nach     dem.     Erkalten wird     sodaalkalisch    gestellt; filtriert  und     mit        Essigsäure    angesäuert.

   Man erhält  das     4-Amino-benzol-Nl-(ss;ss-dimethyl-acroyl)-          sulfonamid.    Aus Alkohol umkristallisiert  bildet es farblose Kristalle vom Schmelz  punkt     184-185 .  



  Process for the production of an aylated sulfonamides.- <B> -_ </B> present patent is a process for the production of the known 4th - Amino-benzene - N1- (ss, ss-dimetliyl-acroyl) - sulfonamide. The process is characterized in that a substituted 4-amino-benzenesulfonamide of the formula
EMI0001.0010
    in which R is a residue that can be split off by hydrolyzing agents,

   converted by saponification into 4-amino-benzene-N, - (ss, ss-dimethyl-acroyl) - sulfonamide.



  The compound forms colorless crystals with a melting point of 184-185. It should be used as a medicine.



  <I> Example 1: </I> 10 parts of N- (4-amino-benzenesulfonyl) - ss, ss-dimethyl-acrylamidine with a melting point of 128-129 and the formula
EMI0001.0028
    are heated to 90-100 for 2 hours with 100 parts of 3.5% hydrochloric acid. After cooling, it is made alkaline with soda, filtered and acidified with acetic acid. The 4-amino-benzene-N, - (ss, ss-dimethyl-acroyl) - sulfonamide is obtained. Recrystallized from alcohol, it forms colorless crystals with a melting point of 184-185.



  <I> Example 2: </I> 10 parts of N- (4-amino-benzenesulfonyl) -ss, ss- dimethyl-acryliminoethyl ether with a melting point of 116 and the formula
EMI0001.0041
         are heated to 90-100 for 2 hours with 200 parts of 2% hydrochloric acid. After cooling, it is made alkaline with soda, filtered and acidified with acetic acid.

   The 4-amino-benzene-Nl- (ss, ss-dimethyl-acroyl) sulfonamide is obtained. Recrystallized from alcohol, it forms colorless crystals with a melting point of 184-185.



  <I> Example 3; </I> 10 parts of N- (4-Amino-benzenesulfonyl) -N'-ethyl-ß, ß-dimethyl-aerylamidine with a melting point of 220-222 of the formula
EMI0002.0013
    are heated to 90-100 for 31/2 hours with 200 parts of 3.5% hydrochloric acid. After this. Cooling is made alkaline to soda; filtered and acidified with acetic acid.

   The 4-amino-benzene-Nl- (ss; ss-dimethyl-acroyl) sulfonamide is obtained. Recrystallized from alcohol, it forms colorless crystals with a melting point of 184-185.

Claims (1)

PATENTANSPRUCH: Verfahren. zur .Herstellung von 4-Amino- benzol - Nl-(ss,ss-dimethyl - acroyl)-sulf onamid, dadurch gekennzeichnet, dass man ein sub stituiertes 4-Amino-benzolsulfonamid der Formel - EMI0002.0033 in der R einen. durch hydrolysierende Mittel abspaltbaren Rest bedeutet, PATENT CLAIM: Process. for .Production of 4-amino-benzene - Nl- (ss, ss-dimethyl - acroyl) sulfonamide, characterized in that a substituted 4-amino-benzenesulfonamide of the formula - EMI0002.0033 in the r one. means residue that can be split off by hydrolyzing agents, durch Verseifung in 4-Amino-benzol-Nl-(ss,ss-dimethyl-acroyl)- sulfonamid überführt. Die Verbindung bildet farblose Kristalle vom Schmelzpunkt 184-185 . Sie soll als Arzneimittel Verwendung finden. UNTERANSPRÜCHE: 1. converted by saponification into 4-amino-benzene-Nl- (ss, ss-dimethyl-acroyl) - sulfonamide. The compound forms colorless crystals with a melting point of 184-185. It should be used as a medicine. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N-(4-Amino- benzolsulfonyl) - ss,ss - dimethyl - acrylamidin durch hydrolytische Spaltung in 4-Amino- benzol - N,- (ss,ss - dimethyl-acroyl)-sulfonamid überführt. 2. Process according to patent claim, characterized in that N- (4-aminobenzenesulfonyl) - ss, ss - dimethyl - acrylamidine by hydrolytic cleavage in 4-aminobenzene - N, - (ss, ss - dimethyl-acroyl) - sulfonamide transferred. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass, man N-(4-Amino- benzolsulfonyl) - ss,ss - dimethyl - acryl - imino- äthyläther durch hydrolytische Spaltung in- 4 - Amino - benzol - N,: Process according to claim, characterized in that, N- (4-amino-benzenesulfonyl) - ss, ss - dimethyl - acrylic - imino - ethyl ether by hydrolytic cleavage in 4 - amino - benzene - N,: - (ss,- - dimethyl -a,cre,yl)- sulfonamid überführt. 3. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man N-(4-Amino- benzolsulfonyl) -N'-äthyl-ss,ss-dimetbyl-acryl- amidin durch hydrolytische Spaltung in 4- Amino -benzol -N1- (ss,ss-dimethyl- acroyl)- sulfonamid überführt. - (ss, - - dimethyl -a, cre, yl) - sulfonamide transferred. 3. The method according to claim, characterized in that N- (4-amino-benzenesulfonyl) -N'-ethyl-ss, ss-dimetbyl-acryl amidine by hydrolytic cleavage in 4-amino-benzene -N1- (ss , ss-dimethyl-acroyl) - sulfonamide transferred.
CH242518D 1943-05-21 1943-05-21 Process for the preparation of an acylated sulfonamide. CH242518A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH242518T 1943-05-21
CH239850T 1944-03-16

Publications (1)

Publication Number Publication Date
CH242518A true CH242518A (en) 1946-05-15

Family

ID=25728447

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242518D CH242518A (en) 1943-05-21 1943-05-21 Process for the preparation of an acylated sulfonamide.

Country Status (1)

Country Link
CH (1) CH242518A (en)

Similar Documents

Publication Publication Date Title
CH242518A (en) Process for the preparation of an acylated sulfonamide.
CH242516A (en) Process for the preparation of an acylated sulfonamide.
CH242522A (en) Process for the preparation of an acylated sulfonamide.
CH242525A (en) Process for the preparation of an acylated sulfonamide.
CH242519A (en) Process for the preparation of an acylated sulfonamide.
CH242527A (en) Process for the preparation of an acylated sulfonamide.
CH242521A (en) Process for the preparation of an acylated sulfonamide.
CH242520A (en) Process for the preparation of an acylated sulfonamide.
CH242523A (en) Process for the preparation of an acylated sulfonamide.
CH242524A (en) Process for the preparation of an acylated sulfonamide.
CH242528A (en) Process for the preparation of an acylated sulfonamide.
CH247620A (en) Process for the preparation of an acylated sulfonamide.
CH242517A (en) Process for the preparation of an acylated sulfonamide.
CH253174A (en) Process for the preparation of an acylated sulfonamide.
CH242526A (en) Process for the preparation of an acylated sulfonamide.
DE439290C (en) Process for the preparation of naphthooxythiophenes
CH242515A (en) Process for the preparation of an acylated sulfonamide.
CH209121A (en) Process for preparing a sulfonic acid amide compound.
DE621582C (en) Process for the preparation of a monooxychrysenic
CH180879A (en) Process for the preparation of an acylated mixture of the isomers of the dihydrofollicle hormone.
CH170447A (en) Process for the production of a monooxychrysenic.
CH238089A (en) Process for the preparation of 4-amino-benzenesulfone-3&#39;-methyl-4&#39;-methylmercapto-benzamide.
CH242291A (en) Process for the preparation of a p-amino-benzenesulfonamide.
CH137210A (en) Process for the preparation of an o-oxybenzyl-aroyl-aminarsinic acid.
CH206622A (en) Method of making a therapeutically useful compound.