CH222732A - 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.

Info

Publication number
CH222732A
CH222732A CH222732DA CH222732A CH 222732 A CH222732 A CH 222732A CH 222732D A CH222732D A CH 222732DA CH 222732 A CH222732 A CH 222732A
Authority
CH
Switzerland
Prior art keywords
benzene
amino
para
derivative
preparation
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 CH222732A publication Critical patent/CH222732A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/76Nitrogen atoms to which a second hetero atom is attached
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides 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
    • C07C311/50Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52Y being a hetero atom
    • C07C311/64X and Y being nitrogen atoms, e.g. N-sulfonylguanidine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/38Nitrogen atoms
    • C07D277/50Nitrogen atoms bound to hetero atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/38Nitrogen atoms
    • C07D277/50Nitrogen atoms bound to hetero atoms
    • C07D277/52Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides

Landscapes

  • 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-benzéne-sulfamide,    ayant la formule  
EMI0001.0004     
    Ce composé connu, qui forme une poudre  blanche et qui fond â 201-2021 C, est sus  ceptible d'application thérapeutique.  



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



  Le produit de la condensation mentionnée  a pour formule  
EMI0001.0009     
    Ce dernier composé est oxydé, par exem  ple par le permanganate de potasse ou des       oxydants    équivalents, en     2(para-nitro-benzène-          sulfa.mido)-thiazol.    On réduit ensuite le groupe  nitro en     amino,    par exemple avec du fer et  de l'acide acétique â     95-100"    selon la mé  thode bien connue de     Béchamp    (A. ch.     [3]    42  190), et on obtient du     2(para-amino-benzène-          sulfamido)-thiazol.     



  Voici des exemples d'exécution du procédé  de l'invention       .Exemple   <I>1:</I>  On dissout 10 gr de     2-amino-thiazol    dans  50     cm'    d'éther sec et on ajoute 6 gr de car  bonate de sodium anhydre. En refroidissant  â 10--15  , on ajoute alors lentement une  solution de 14 gr de     p-nitro-benzène-chlorure     
EMI0001.0023     
  
    de <SEP> soufre
<tb>  <B><I>(02N- < D-SCI)</I></B>       dans 100 cm' d'éther séché, en agitant bien  le mélange. Un précipité résineux est formé.  Après une heure, on ajoute 100     cm3    d'eau en  agitant et ensuite on sépare le précipité de  l'eau et de l'éther.

        Ce composé a la formule  
EMI0002.0001     
    La réaction peut aussi être mise en     oeuvre     en solution     benzénique.     



  Pour l'oxydation de ce dernier composé  en dérivé     sulfamido,    1 gr de la matière brute  est dissous dans 15 cm" de     dioxane    et cette  solution est diluée par 5     cm3    d'eau. Cette  solution étant refroidie à     10-150,    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 10     0;'o     et décoloré par un peu de bisulfite de sodium.  Le précipité est séparé par filtration.

   Il con  siste en     2(para-nitro-benzène-sulfamido)-thia-          zol.     



  10 gr de ce composé nitré brut sont ver  sés dans un mélange bien agité de 100 gr  de limaille de fer et de 300 cm' d'acide acé  tique à une température de 95-100 0. Après  une heure d'agitation à 95 0, le mélange est       refroidi    à 20 " et rendu alcalin avec une solu  tion de soude caustique. Le mélange est filtré  et le filtrat acidifié à l'acide acétique. Le pré  cipité est filtré. Il consiste en     2(para-amino-          benzène-sulfamido)-thiazol    et fond à 201 à  2020.    <I>Exemple 2:</I>    5 gr de     2-aniino-thiazol    sont dissous dans  30     cm'    de     pyridine    sèche.

   On ajoute à cette  solution en refroidissant à 10-15 0 et agitant,  9,5 gr de     p-iiitro-benzèrie-chlorure    de soufre  
EMI0002.0019     
    Après une     heure    de repos à 20 0, la solution  jaune est versée dans 500     emg    d'eau. Le pré  cipité est filtré et séché. Après     recristallisa-          tion    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 0 un petit excès de perman  ganate de potasse.

   Le mélange est     alors    versé  dans 100 cm' d'acide sulfurique     10'1/o    et déco  loré à l'aide de bisulfite de sodium. Le pré  cipité est filtré. Par réduction selon l'exemple  1, on obtient du     2(para-amino-benzéne-sulf-          amido)-thiazol.  



  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-benzenesulfonamide, having the formula
EMI0001.0004
    This known compound, which forms a white powder and which melts at 201-2021 C, is susceptible to therapeutic application.



  According to the present invention, the above-mentioned compound is prepared as follows: 2-amino-thiazol 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
EMI0001.0009
    The latter compound is oxidized, for example by potassium permanganate or equivalent oxidants, to 2 (para-nitro-benzene-sulfa.mido) -thiazol. The nitro group is then reduced to amino, for example with iron and 95-100 "acetic acid according to the well-known method of Béchamp (A. ch. [3] 42 190), and 2 (para-amino-benzene-sulfamido) -thiazol.



  Here are examples of execution of the process of the invention. Example <I> 1: </I> 10 g of 2-amino-thiazol are dissolved in 50 cm 3 of dry ether and 6 g of car bonate of sodium anhydrous. While cooling to 10--15, a solution of 14 g of p-nitro-benzene-chloride is then slowly added.
EMI0001.0023
  
    of <SEP> sulfur
<tb> <B> <I> (02N- <D-SCI) </I> </B> in 100 cm 'of dried ether, stirring the mixture well. A resinous precipitate is formed. After one hour, 100 cm3 of water are added with stirring and then the precipitate is separated from the water and ether.

        This compound has the formula
EMI0002.0001
    The reaction can also be carried out in benzene solution.



  For the oxidation of the latter compound to a sulfamido derivative, 1 g of the crude material is dissolved in 15 cm 3 of dioxane and this solution is diluted with 5 cm 3 of water. This solution being cooled to 10-150, it is added. stir while slowly adding powdered 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 sulfuric acid 10% and decolorized with a little sodium bisulphite The precipitate is separated by filtration.

   It consists of 2 (para-nitro-benzene-sulfamido) -thia-zol.



  10 g of this crude nitrated 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 95-100 0. After stirring for one hour at 95 0 , the mixture is cooled to 20 "and made alkaline with caustic soda solution. The mixture is filtered and the filtrate acidified with acetic acid. The precipitate is filtered. It consists of 2 (para-amino-benzene- sulfamido) -thiazol and melts at 201 to 2020. <I> Example 2: </I> 5 g of 2-aniino-thiazol are dissolved in 30 cm 3 of dry pyridine.

   Is added to this solution while cooling to 10-15 0 and stirring, 9.5 g of p-iiitro-benzenesulfur chloride
EMI0002.0019
    After standing at 20 ° for one hour, the yellow solution is poured into 500 emg of water. The precipitate is filtered 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. With stirring, a small excess of potassium hydroxide permanence is added slowly to 10-15 °.

   The mixture is then poured into 100 cm 3 of 10'1 / o sulfuric acid and decolorized with sodium bisulphite. The precipitate is filtered. By reduction according to Example 1, 2 (para-amino-benzenesulfamido) -thiazol is obtained.

 

Claims (1)

REVENDICATION Procédé de préparation d'un dérivé de la para-amino-benzène-sulfamide, caractérisé en ce que l'on fait réagir du 2-amino-thiazol avec un p-nitro-benzène-halogénure de soufre de formule EMI0002.0031 pour former le composé de formule EMI0002.0032 puis en ce que l'on soumet ce dernier composé à une oxydation de façon à obtenir le 2(p- nitro-benzène-sulfamido)-thiazol, que l'on sou met à une réduction pour obtenir le 2(para- amino-benzène-sulfamido)-thiazol. CLAIM Process for the preparation of a derivative of para-amino-benzene-sulfonamide, characterized in that 2-amino-thiazol is reacted with a p-nitro-benzene-sulfur halide of formula EMI0002.0031 to form the compound of formula EMI0002.0032 then in that the latter compound is subjected to oxidation so as to obtain 2 (p-nitro-benzene-sulfamido) -thiazol, which is subjected to reduction to obtain 2 (para-amino- benzene-sulfamido) -thiazol.
CH222732D 1941-08-08 1941-08-08 Process for the preparation of a derivative of para-amino-benzene-sulfonamide. CH222732A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH222732T 1941-08-08
CH220046T 1941-08-08

Publications (1)

Publication Number Publication Date
CH222732A true CH222732A (en) 1942-07-31

Family

ID=25726386

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222732D CH222732A (en) 1941-08-08 1941-08-08 Process for the preparation of a derivative of para-amino-benzene-sulfonamide.

Country Status (1)

Country Link
CH (1) CH222732A (en)

Similar Documents

Publication Publication Date Title
CH398887A (en) X-ray contrast agent
CH222732A (en) Process for the preparation of a derivative of para-amino-benzene-sulfonamide.
CH222734A (en) Process for the preparation of a derivative of para-amino-benzene-sulfonamide.
CH222733A (en) Process for the preparation of a derivative of para-amino-benzene-sulfonamide.
EP0004257B1 (en) Benzonitrile derivative, process for its preparation and its application
CH220046A (en) Process for the preparation of a derivative of para-amino-benzene-sulfonamide.
CH222735A (en) Process for the preparation of a derivative of para-amino-benzene-sulfonamide.
EP0627403B1 (en) Method for the production of hydroxyphenylacetic acids
CH297837A (en) Process for preparing 1-chloro-4-methylthiaxanthone.
CH370093A (en) Process for the preparation of diamino-caproic acid derivatives
CH237879A (en) Process for the preparation of -dimethyl-ss-cyclohexylethylamine.
CH268051A (en) Process for preparing 1-methyl-4-piperazine-N, N-diethyl-carboxamide.
CH396030A (en) Process for the preparation of N-isopropyl-N-benzyl-hydrazine and its salts
CH326417A (en) Process for preparing geranyl acetone
CH307324A (en) A process for preparing amino-2-hydroxy-4- (chloro-4&#39;-phenyl) -5-ethyl-6-pyrimidine.
CH286752A (en) A process for the preparation of a fully acylated aromatic aminodiol, nitrated in the nucleus.
CH299940A (en) Process for the preparation of a pyrimidine derivative.
CH329255A (en) Process for the preparation of aryl-triamino-sulfamic acids and their salts
CH271931A (en) Process for preparing 2-bromo-2-formyl-ethyl-pyridinium bromide.
CH205679A (en) Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.
CH207309A (en) Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.
CH286745A (en) A process for preparing an aromatic diacylated hydroxy-amino-ketone.
CH377837A (en) Process for the preparation of unsaturated derivatives of the reserpine series
CH286751A (en) A process for the preparation of a fully acylated aromatic aminodiol, nitrated in the nucleus.
CH357384A (en) Process for preparing 5,5&#39;-dinitro-2,2&#39;-dichlorobenzil