CH222733A - Process for the preparation of a derivative of para-amino-benzene-sulfonamide. - Google Patents

Process for the preparation of a derivative of para-amino-benzene-sulfonamide.

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Publication number
CH222733A
CH222733A CH222733DA CH222733A CH 222733 A CH222733 A CH 222733A CH 222733D A CH222733D A CH 222733DA CH 222733 A CH222733 A CH 222733A
Authority
CH
Switzerland
Prior art keywords
benzene
amino
para
sulfonamide
derivative
Prior art date
Application number
Other languages
French (fr)
Inventor
Chemisches Industrielles Cilag
Original Assignee
Cilag Chemisches Ind Lab A G
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 A G filed Critical Cilag Chemisches Ind Lab A G
Publication of CH222733A publication Critical patent/CH222733A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • 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
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/64—X and Y being nitrogen atoms, e.g. N-sulfonylguanidine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/50—Nitrogen atoms bound to hetero atoms
    • C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Procédé de préparation d'un dérivé de la     para-amino-benzène-sulfamide.       La présente invention a pour objet un  procédé de préparation d'un dérivé de la     para-          amino-benzène-sulfamide,    ayant la formule  
EMI0001.0004     
    Ce composé connu, qui forme une poudre  blanche et qui fond à<B>255-2561</B> C, est sus  ceptible d'application thérapeutique.  



  Selon la présente invention, le composé  mentionné ci-dessus est préparé comme suit:  On condense de la     2-amino-pyrimidine    avec  un     p-nitro-benzène-halogénure    de soufre, ayant  pour formule  
EMI0001.0007     
    Ce dernier composé est facile à préparer  d'après     Zincke    A. 400 9.  



  Le produit de la condensation mentionnée  a pour     formule     
EMI0001.0010     
    Ce dernier composé est oxydé, par exem  ple par le permanganate de potasse ou des       oxydants    équivalents, en     2(para-nitro-benzène-          sulfamido)-pyrimidine.     



  On réduit ensuite le groupe nitro en     amillo,     par exemple avec du fer et de l'acide acéti  que à 95-100   selon la méthode bien con  nue de     Béchamp    (A. ch.     [3]    42 190), et on  obtient de la     2(para-amino-benzèlle-sulfamido)-          pyrimidine.     



  Voici des exemples d'exécution du procédé  de l'invention       Exemple   <I>1:</I>  On dissout 9,5 gr de     2-amino-pyrimidine     dans 50 cm' d'éther sec et on ajoute 6 gr  de carbonate de sodium anhydre. En refroi  dissant à 10-15  , on ajoute alors lentement      une solution de 14 gr de     p-nitro-beiizérie-          chlorure    de soufre  
EMI0002.0003     
    dans 100 cm' d'éther séché, en agitant bien  le mélange. Un précipité résineux est     formé.     Après une heure, on ajoute 100     eni''        d'eau     en     agitant    et ensuite on sépare le précipité  de     l'eau    et de l'éther.  



  Ce composé a la formule  
EMI0002.0009     
    La réaction peut aussi être mise en     oeuvre     en solution     benzénique.     



       Pour    l'oxydation de ce dernier composé  en     dérivé        sulfamide,    1 gr de la matière brute  est dissous dans 15 cm' de     dioxane    et cette  solution est diluée par 5     cni3    d'eau. Cette  solution étant refroidie à<B>10-15',</B> on l'agite  tout en     ajoutant    lentement du     permanganate     de potasse pulvérisé jusqu'à ce qu'un petit  excès de cet oxydant soit présent et     que    la       solution    reste rouge. Le mélange est ensuite  versé dans 100 cm' d'acide sulfurique<B>10\</B> /0  et décoloré par un peu de bisulfite de sodium.  Le précipité est séparé par filtration.

   IL con  siste en     2(par < i-nitro-benzène-sulf < iinido)-pyi-i-          midine.     



  10 gr de ce composé nitré brut sont versés  dans un     mélange    bien agité de 100 gr de       limaille    de fer et de 300 cm" d'acide acétique  à une température de     95-1000.    Après une  heure d'agitation à<B>950,</B> le mélange est  refroidi à 20 0 et rendu alcalin avec une solu  tion de soude caustique. Le mélange est filtré  et le filtrat acidifié à l'acide acétique. Le  précipité est filtré.     Il    consiste en     2(para-ainino-          benzène-sulf@imido)-pyrimidine    et fond à 255  à 256 0.  



       Exemple   <I>2:</I>  4,75 gr de     2-amino-pyrimidine    sont dissous  dans 30 cm' de     pyridine    sèche. On ajoute à    cette solution en refroidissant à<B>10-150</B> et  agitant 9,5 gr de     p-nitro-benzène-chlorure    de  soufre  
EMI0002.0033     
    Après une heure de repos à 200, la solution  jaune est versée dans 500 cm" d'eau. Le  précipité est filtré et séché. Après recristal  lisation à l'alcool ou au benzène, le composé       obtenu    est oxydé à la manière suivante:  1 gr du composé obtenu ainsi est dissous  dans 50     cm'    d'acétone. La solution est diluée  par 10 cm" d'eau.

   En agitant, on ajoute len  tement à     10-15')    un petit excès de perman  ganate de potasse. Le mélange est alors versé       dans        100        cm"        d'acide        sulfurique        10        %        et        déco-          loré    à l'aide de     bisulfite    de sodium.

   Le pré  cipité est     filtré.        Par    réduction selon exemple  1 on     obtient    de la     2(1,')ar,@i.- < iaziitio-bezizêne-sulf-          amidü)-pyrimidine.  



  Process for the preparation of a derivative of para-amino-benzene-sulfonamide. The present invention relates to a process for the preparation of a derivative of para-amino-benzene-sulfonylurea, having the formula
EMI0001.0004
    This known compound, which forms a white powder and melts at <B> 255-2561 </B> C, is susceptible to therapeutic application.



  According to the present invention, the above-mentioned compound is prepared as follows: 2-amino-pyrimidine is condensed with a p-nitro-benzene-sulfur halide, having the formula
EMI0001.0007
    The latter compound is easy to prepare according to Zincke A. 400 9.



  The product of the mentioned condensation has the formula
EMI0001.0010
    The latter compound is oxidized, for example by potassium permanganate or equivalent oxidants, to 2 (para-nitro-benzene-sulfamido) -pyrimidine.



  The nitro group is then reduced to amillo, for example with iron and acetic acid to 95-100 according to the well-known method of Béchamp (A. ch. [3] 42 190), and we obtain 2 (para-amino-benzelll-sulfamido) - pyrimidine.



  Here are examples of execution of the process of the invention Example <I> 1: </I> 9.5 g of 2-amino-pyrimidine are dissolved in 50 cm 3 of dry ether and 6 g of carbonate are added. sodium anhydrous. While cooling to 10-15, then slowly add a solution of 14 g of p-nitro-beiizérie-sulfur chloride
EMI0002.0003
    in 100 cm 3 of dried ether, stirring the mixture well. A resinous precipitate is formed. After one hour, 100 ml of water are added with stirring and then the precipitate is separated from water and ether.



  This compound has the formula
EMI0002.0009
    The reaction can also be carried out in benzene solution.



       For the oxidation of the latter compound to a sulfonamide derivative, 1 g of the crude material is dissolved in 15 cm 3 of dioxane and this solution is diluted with 5 cc of water. This solution being cooled to <B> 10-15 ', </B> it is stirred while slowly adding pulverized potassium permanganate until a small excess of this oxidant is present and the solution remains red. . The mixture is then poured into 100 cm 3 of <B> 10 \ </B> / 0 sulfuric acid and decolorized with a little sodium bisulfite. The precipitate is separated by filtration.

   It consists of 2 (per <i-nitro-benzene-sulf <iinido) -pyi-i-midine.



  10 g of this crude nitro compound are poured into a well-stirred mixture of 100 g of iron filings and 300 cm 3 of acetic acid at a temperature of 95-1000. After stirring for one hour at <B> 950, </B> the mixture is cooled to 20 0 and made alkaline with a solution of caustic soda. The mixture is filtered and the filtrate acidified with acetic acid. The precipitate is filtered. It consists of 2 (para-ainino- benzene-sulf (imido) -pyrimidine and melts at 255-256 0.



       Example <I> 2: </I> 4.75 g of 2-amino-pyrimidine are dissolved in 30 cm 3 of dry pyridine. Add to this solution while cooling to <B> 10-150 </B> and stirring 9.5 g of p-nitro-benzene-sulfur chloride
EMI0002.0033
    After standing at 200 for one hour, the yellow solution is poured into 500 cm 3 of water. The precipitate is filtered off and dried. After recrystallization with alcohol or benzene, the compound obtained is oxidized as follows: 1 g of the compound thus obtained is dissolved in 50 cm 3 of acetone. The solution is diluted with 10 cm 3 of water.

   While stirring, a small excess of potassium hydroxide permanence is added slowly to 10-15%. The mixture is then poured into 100 cm 3 of 10% sulfuric acid and decolourised with sodium bisulfite.

   The precipitate is filtered. By reduction according to Example 1, 2 (1, ') ar, @ i.- <iaziitio-bezizene-sulf-amidü) -pyrimidine is obtained.

Claims (1)

REVENDICATION Procédé de préparation d'un dérivé de la para-amino-henzéne-sulfamide, caractérisé en ce que l'on fait réagir de la 2-amino-pyrimi- dine avec un p-nitro-benzène-halogénure de soufre de formule EMI0002.0060 pour former le composé de formule EMI0002.0061 puis en ce que l'on soumet ce dernier com posé à une oxydation de faon â obtenir la 2(h-nitro-benzène-sulfamido)-pyrimidine, que l'on soumet à une réduction pour obtenir la 2 (p ara-amino - benzène - sulfamide) CLAIM Process for preparing a derivative of para-amino-henzene-sulfonamide, characterized in that 2-amino-pyrimidine is reacted with a p-nitro-benzene-sulfur halide of formula EMI0002.0060 to form the compound of formula EMI0002.0061 then in that the latter compound is subjected to oxidation so as to obtain 2 (h-nitro-benzene-sulfamido) -pyrimidine, which is subjected to reduction to obtain 2 (p ara-amino - benzene - sulfonamide) - pyrimidine. - pyrimidine.
CH222733D 1941-08-08 1941-08-08 Process for the preparation of a derivative of para-amino-benzene-sulfonamide. CH222733A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH220046T 1941-08-08
CH222733T 1941-08-08

Publications (1)

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CH222733A true CH222733A (en) 1942-07-31

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CH222733D CH222733A (en) 1941-08-08 1941-08-08 Process for the preparation of a derivative of para-amino-benzene-sulfonamide.

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CH (1) CH222733A (en)

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