CH234975A - Process for the preparation of a sulfonamide. - Google Patents

Process for the preparation of a sulfonamide.

Info

Publication number
CH234975A
CH234975A CH234975DA CH234975A CH 234975 A CH234975 A CH 234975A CH 234975D A CH234975D A CH 234975DA CH 234975 A CH234975 A CH 234975A
Authority
CH
Switzerland
Prior art keywords
sulfonylamino
acylaminobenzene
pyrimidine
dimethyl
preparation
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 CH234975A publication Critical patent/CH234975A/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

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

Description

  

  Verfahren zur Darstellung eines Sulfonamides.    Gegenstand der Erfindung ist ein eigen  artiges Verfahren zur Darstellung eines Sul  fonamides,     nämlich    des bisher nicht bekann  ten 2-(p-     Aminobenzol-sulfonylamino-)4,6-di-          methyl-pyrimidins,    welches als Heilmittel  gegen Infektionen verwendet werden soll.  



  Das Verfahren ist dadurch gekennzeich  net, dass man ein     p-Acylaminobenzol-sulfonyl-          guanidin    mit     Acetylaceton    zum 2-(p-Acyl       aminobenzol-sulfonylamino-)4,6-dimethyl-py-          rimidin    kondensiert und daraus durch Ab  spaltung des     Acrylrestes    das     2-(p-Aminoben-          zol    -     sulfonylamino-)    4,6 -     dimethyl    -     pyrimidin          gewinnt.     



       .Eine        Lösung        Ausführungsbeispiel:        von        25,6g        Acetylaminoben-          zol-sulfonyl-guanidin    in 100 cm' absolutem  Alkohol     wird    mit 10g     Acetylaceton    versetzt  und das Gemisch 10 Stunden am     Rückfluss-          kühler    gekocht.

   Der Alkohol wird wegdestil  liert und das zurückbleibende 2-(p-Acetyl       a.minobenzol-sulfonylamino-)4,6-dimethyl-py-          rimidin    aus Wasser umkristallisiert, dann    zwecks Abspaltung des     Acylrestes    1     Stunde     mit     7prozentiger    Salzsäure verkocht. Beim  Neutralisieren der Lösung fällt das 2 -     (p-          Aminobenzol    -     sulfonylamino-)    4,6 -     dimethyl-          pyrimidin    in weissen Kristallen aus. Die  neue Verbindung schmilzt bei 176 bis l80 .

    Ausbeute: 24,5 g oder 88,3     %    d.     Th.     



  An Stelle von absolutem Alkohol können  auch andere wasserbindende Mittel, zum Bei  spiel konzentrierte Schwefelsäure, verwendet  werden.



  Process for the preparation of a sulfonamide. The invention relates to a peculiar method for the preparation of a Sul fonamides, namely the previously unknown 2- (p-aminobenzene-sulfonylamino) 4,6-dimethyl-pyrimidine, which is to be used as a remedy for infections.



  The process is characterized in that a p-acylaminobenzene-sulfonyl-guanidine is condensed with acetylacetone to form 2- (p-acyl aminobenzene-sulfonylamino-) 4,6-dimethyl-pyrimidine and, by splitting off the acrylic residue, the 2 - (p-aminobenzene - sulfonylamino-) 4,6 - dimethyl - pyrimidine wins.



       A solution, exemplary embodiment: 10 g of acetylacetone are added to 25.6 g of acetylaminobenzene-sulfonyl-guanidine in 100 cm of absolute alcohol and the mixture is boiled for 10 hours on a reflux condenser.

   The alcohol is distilled off and the remaining 2- (p-acetyl a.minobenzene-sulfonylamino-) 4,6-dimethyl-pyrimidine is recrystallized from water, then boiled for 1 hour with 7 percent hydrochloric acid to split off the acyl residue. When the solution is neutralized, the 2 - (p-aminobenzene-sulfonylamino) 4,6-dimethylpyrimidine precipitates out in white crystals. The new compound melts at 176-180.

    Yield: 24.5 g or 88.3% of theory. Th.



  Instead of absolute alcohol, other water-binding agents, for example concentrated sulfuric acid, can also be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Sulfon amids, dadurch gekennzeichnet, dass man ein p - Acylaminobenzol - sulfonyl - guanidin mit Acetylaceton zum 2-(p-Acylaminobenzol-sul- fonylamino-)4,6-dimethyl-pyrimidin konden siert und daraus durch Abspaltung des Acyl- restes das 2-(p-..Aminobenzol-sulfonylamino-)- 4,6-dimethyl-pyrimidin gewinnt. Das farblose Verfahrensprodukt schmilzt bei<B>176</B> bis 180 . Es soll als Heilmittel gegen Infektionen verwendet werden. <B>UNTERANSPRÜCHE:</B> 1. PATENT CLAIM: Process for the preparation of a sulfonamide, characterized in that a p-acylaminobenzene-sulfonyl-guanidine is condensed with acetylacetone to form 2- (p-acylaminobenzene-sulfonylamino-) 4,6-dimethyl-pyrimidine and condensed therefrom by cleavage of the acyl residue, the 2- (p - .. aminobenzene-sulfonylamino -) - 4,6-dimethyl-pyrimidine wins. The colorless process product melts at <B> 176 </B> to 180. It is said to be used as a remedy for infections. <B> SUBClaims: </B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man die Konden sation von p- Acylaminobenzol-sulfonyl-guani- din mit Acetylaceton in Gegenwart eines was- serbindenden Mittels ausführt. ?. Verfahren nach Unteransprueh 1., da durch gel@exxnzeiehnet., dass man die Konden sation in Gegenkart von absolutem Alkobol ausfübrt. Process according to patent claim, characterized in that the condensation of p-acylaminobenzene-sulfonyl-guanidine with acetylacetone is carried out in the presence of a water-binding agent. ?. Method according to sub-claim 1., because gel @ exxnzeiehnet. That the condensation is carried out in the counterpart of absolute alcohol.
CH234975D 1942-02-19 1942-02-19 Process for the preparation of a sulfonamide. CH234975A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH234975T 1942-02-19
CH226118T 1943-08-20

Publications (1)

Publication Number Publication Date
CH234975A true CH234975A (en) 1944-10-31

Family

ID=25726963

Family Applications (1)

Application Number Title Priority Date Filing Date
CH234975D CH234975A (en) 1942-02-19 1942-02-19 Process for the preparation of a sulfonamide.

Country Status (1)

Country Link
CH (1) CH234975A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960098C (en) * 1953-12-22 1957-03-14 Nordmark Werke Gmbh Process for the preparation of 2-benzenesulfonamido-4-methyl-6-oxy-pyrimidines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960098C (en) * 1953-12-22 1957-03-14 Nordmark Werke Gmbh Process for the preparation of 2-benzenesulfonamido-4-methyl-6-oxy-pyrimidines

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