CH239702A - Process for the preparation of a sulfonamide. - Google Patents

Process for the preparation of a sulfonamide.

Info

Publication number
CH239702A
CH239702A CH239702DA CH239702A CH 239702 A CH239702 A CH 239702A CH 239702D A CH239702D A CH 239702DA CH 239702 A CH239702 A CH 239702A
Authority
CH
Switzerland
Prior art keywords
sep
sulfonamide
preparation
benzene
dimethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Cilag Chemisch Laboratorium
Original Assignee
Cilag Chemisches Ind Lab 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 Cilag Chemisches Ind Lab Ag filed Critical Cilag Chemisches Ind Lab Ag
Publication of CH239702A publication Critical patent/CH239702A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines

Landscapes

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

Description

  

      Verfahren    zur Darstellung eines Sulfonamides.  
EMI0001.0002     
  
    Das <SEP> in <SEP> der <SEP> Medizin <SEP> als <SEP> antibakterielles
<tb>  Mittel <SEP> bekannt <SEP> gewordene <SEP> 2-(p-Aminobenz:ol  sulfon3#lamino) <SEP> - <SEP> 4,6 <SEP> - <SEP> dimethyl <SEP> - <SEP> pyrimidin <SEP> üt
<tb>  infolge <SEP> seiner <SEP> igeringen <SEP> Löslichkeit <SEP> zu <SEP> intra  venäsen <SEP> Injektionen <SEP> wenig <SEP> geeignet. <SEP> Man <SEP> ist
<tb>  daheTdazu <SEP> übergegangen, <SEP> an <SEP> seiner <SEP> Stehle
<tb>  .die <SEP> in <SEP> Wasser <SEP> viel <SEP> ileichter <SEP> und <SEP> mit <SEP> neutraler
<tb>  Reaktion <SEP> löslichen <SEP> Alkalisalze <SEP> des <SEP> <B>2-(p-N</B>4<B>_</B>
<tb>  Succinyl-amino#b:

  enzol-su <SEP> #lfonylamino)-4,6-di  methyl-pyrimidins <SEP> zu <SEP> verwenden. <SEP> Das <SEP> .diesen
<tb>  Seilzen <SEP> zu <SEP> runde <SEP> liegende <SEP> Sulfonamid <SEP> ist
<tb>  bisher <SEP> @durch <SEP> Befiand@lung <SEP> von <SEP> 2-(p-Amino  benzoT@-ssulfanyJamino@) <SEP> -4,6 <SEP> - <SEP> dim@ethyl-pyrimi  Jin <SEP> mit <SEP> Bernste:insäureauhydrid <SEP> gewonnen
<tb>  worden.
<tb>  



  Gegenstand <SEP> der <SEP> vorliegenden <SEP> Erfindung
<tb>  ist <SEP> ein <SEP> in <SEP> seiner <SEP> Art <SEP> neues <SEP> Verfahren <SEP> zur <SEP> Dar  stellung <SEP> des <SEP> 2-(p-N4-Suecinyl-aminobenzol  sulf <SEP> onylamino <SEP> )-4, <SEP> 6-dimethyl-py <SEP> rimidins, <SEP> wei  ehes <SEP> dadurch <SEP> gekennzeichnet <SEP> ist, <SEP> @dass <SEP> man <SEP> p  Succinylamino-benzol-sulfornylguanidin <SEP> mit
<tb>  A.eetylaceto:n <SEP> kondensiert. <SEP> Die <SEP> I#ondensation
<tb>  kann. <SEP> durch <SEP> Erhitzen, <SEP> einer <SEP> innigen <SEP> Mischung       ,der     beiden.    Ausgangsstoffe auf eine Tempe  ratur von     wenigstens    120' C durchgeführt  werden.  



  <I>Aas f</I>     ührwngsbeispiel:     Ein inniges     Gemisch    von 31,5 g     p-Succinyl-          amino    - Benzol -     sulfonylbo^uanidin    und 35 g       Acetylacetan    wird im Druckgefäss unter Rüh  ren 3     @Stunden    auf 140 bis<B>160'</B> C erhitzt.       Damauf    wird das     überschüssige        Acetylaeeton          abdestilliert    und der Rückstand aus 6 n.

   Essig  säure umkristallisiert.     Ausbeute:    35 g oder       92,69o'    d.     Th.    Das so     .erhaltene        2-(p-N4-          Succinylamino,-benzol-sulf        onylamino)    - 4, 6-     di-          methyl-pyrimidin    zeigt,     in        Übereinstimmung     ,mit dem     Schrifttum,    einen     Schmelzpunkt     (u.     Zers.)    von 226  C.



      Process for the preparation of a sulfonamide.
EMI0001.0002
  
    The <SEP> in <SEP> of <SEP> medicine <SEP> as <SEP> antibacterial
<tb> Medium <SEP> known <SEP> <SEP> 2- (p-aminobenz: ol sulfon3 # lamino) <SEP> - <SEP> 4,6 <SEP> - <SEP> dimethyl <SEP> - < SEP> pyrimidine <SEP> üt
<tb> due to <SEP> its <SEP> low <SEP> solubility <SEP> for <SEP> intravenous <SEP> injections <SEP> not very suitable <SEP>. <SEP> Man <SEP> is
<tb> daheT to <SEP> passed over, <SEP> to <SEP> his <SEP> steals
<tb> .the <SEP> in <SEP> water <SEP> much <SEP> ole easier <SEP> and <SEP> with <SEP> more neutral
<tb> Reaction <SEP> soluble <SEP> alkali salts <SEP> of <SEP> <B> 2- (p-N </B> 4 <B> _ </B>
<tb> succinyl-amino # b:

  Use enzol-su <SEP> #lfonylamino) -4,6-dimethyl-pyrimidins <SEP> for <SEP>. <SEP> The <SEP> .this
<tb> Seilzen <SEP> to <SEP> round <SEP> lying <SEP> sulfonamide <SEP> is
<tb> so far <SEP> @by <SEP> Befiand @ lung <SEP> from <SEP> 2- (p-Amino benzoT @ -ssulfanyJamino @) <SEP> -4,6 <SEP> - <SEP> dim @ ethyl-pyrimi Jin <SEP> with <SEP> amber: obtained insäureauhydrid <SEP>
<tb> been.
<tb>



  Subject <SEP> of the <SEP> present <SEP> invention
<tb> is <SEP> a <SEP> in <SEP> of its <SEP> type <SEP> new <SEP> method <SEP> for <SEP> display <SEP> of <SEP> 2- (p-N4 -Suecinyl-aminobenzol sulf <SEP> onylamino <SEP>) -4, <SEP> 6-dimethyl-py <SEP> rimidins, <SEP> because <SEP> is marked with <SEP>, <SEP> @that <SEP> one <SEP> p succinylamino-benzene-sulfornylguanidine <SEP> with
<tb> A.eetylaceto: n <SEP> condensed. <SEP> The <SEP> I # ondensation
<tb> can. <SEP> by <SEP> heating, <SEP> a <SEP> intimate <SEP> mixture of the two. Starting materials are carried out to a temperature of at least 120 ° C.



  <I> Aas f </I> ührwngsbeispiel: An intimate mixture of 31.5 g of p-succinylamino - benzene - sulfonylbo ^ uanidine and 35 g of acetylacetane is stirred in a pressure vessel for 3 hours to 140 to 160 '</B> C heated. Then the excess Acetylaeeton is distilled off and the residue from 6 n.

   Acetic acid recrystallized. Yield: 35 g or 92.69o 'd. The 2- (p-N4-succinylamino, -benzene-sulfonylamino) -4, 6- dimethyl-pyrimidine obtained in this way shows, in accordance with the literature, a melting point (and decomposition) of 226 C.

Claims (1)

PATENTANSPRUCH: EMI0001.0030 Verfahren <SEP> zur <SEP> Darstellung <SEP> -eines <SEP> Sulfon amides, <SEP> dadurch <SEP> gekennzeichnet, <SEP> @dass <SEP> man <SEP> p Succinylarmino,-benzol-sulfo@nyl-guanidin <SEP> mit <tb> A@eetyla"ceton <SEP> zum <SEP> 2-(p-N4-Succinylannine- EMI0002.0001 henzol <SEP> - <SEP> sulfony <SEP> lamino) <SEP> - <SEP> 4,G <SEP> - <SEP> dimethy <SEP> l <SEP> - <SEP> pyri midin <SEP> kondensiert. <tb> UNTERANSPRUCH: <tb> Verfahren <SEP> nach <SEP> Patentansprueh, <SEP> dadureh <tb> 5 <SEP> gekennzeiehuet, <SEP> dass <SEP> man <SEP> eine <SEP> l1-Iisehung <SEP> der EMI0002.0002 beiden <SEP> Aus.#an#sstoff'e <SEP> auf <SEP> eine <SEP> Temperatur <tb> von <SEP> mindestens <SEP> 120" <SEP> C <SEP> erhitzt. PATENT CLAIM: EMI0001.0030 Method <SEP> for <SEP> representation <SEP> -a <SEP> sulfon amide, <SEP> characterized by <SEP>, <SEP> @that <SEP> one <SEP> p succinylarmino, -benzene-sulfo @ nyl -guanidine <SEP> with <tb> A @ eetyla "ceton <SEP> to <SEP> 2- (p-N4-Succinylannine- EMI0002.0001 henzol <SEP> - <SEP> sulfony <SEP> lamino) <SEP> - <SEP> 4, G <SEP> - <SEP> dimethy <SEP> l <SEP> - <SEP> pyri midin <SEP> condensed. <tb> SUBClaim: <tb> Method <SEP> according to <SEP> patent claim, <SEP> dadureh <tb> 5 <SEP> marked, <SEP> that <SEP> man <SEP> a <SEP> l1-Iisehung <SEP> of EMI0002.0002 both <SEP> off. # on # sstoff'e <SEP> on <SEP> a <SEP> temperature <tb> by <SEP> at least <SEP> 120 "<SEP> C <SEP> heated.
CH239702D 1943-08-20 1943-08-20 Process for the preparation of a sulfonamide. CH239702A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH239702T 1943-08-20
CH226118T 1943-08-20

Publications (1)

Publication Number Publication Date
CH239702A true CH239702A (en) 1945-10-31

Family

ID=25726970

Family Applications (1)

Application Number Title Priority Date Filing Date
CH239702D CH239702A (en) 1943-08-20 1943-08-20 Process for the preparation of a sulfonamide.

Country Status (1)

Country Link
CH (1) CH239702A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2466456A1 (en) * 1979-09-27 1981-04-10 Niviere Pierre Soluble antibacterial sulphonamide derivs. - prepd. from a sulphonamide, an aldehyde and a di:carboxylic acid mono:amide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2466456A1 (en) * 1979-09-27 1981-04-10 Niviere Pierre Soluble antibacterial sulphonamide derivs. - prepd. from a sulphonamide, an aldehyde and a di:carboxylic acid mono:amide

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