CH218231A - Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol. - Google Patents

Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol.

Info

Publication number
CH218231A
CH218231A CH218231DA CH218231A CH 218231 A CH218231 A CH 218231A CH 218231D A CH218231D A CH 218231DA CH 218231 A CH218231 A CH 218231A
Authority
CH
Switzerland
Prior art keywords
para
amino
thiazol
benzene
sulfamido
Prior art date
Application number
Other languages
French (fr)
Inventor
Rhone-Poulenc Societ Chimiques
Original Assignee
Rhone Poulenc Chemicals
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 Rhone Poulenc Chemicals filed Critical Rhone Poulenc Chemicals
Publication of CH218231A publication Critical patent/CH218231A/en

Links

Classifications

    • 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

Landscapes

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

Description

  

  Procédé de préparation du     2-(para-amino-benzène-sulfamido)-thiazol.       La présente invention a pour objet un  procédé .de préparation du     2-(para-amino-          benzène-sulfamido)-thi.a7,ol,    ayant pour for  mule:  
EMI0001.0004     
    Ce composé fond à 196-197   C. Il est peu  soluble     dans    l'eau, il     présente        des        propriétés     bactéricides     marquantes    et est susceptible  d'application &  thérapeutiques..  



  Le procédé selon l'invention est     caracté-          risé    en ce que l'on fait réagir .du     2-amino-          thiazol    avec un     halogénure    de     para-ha        logéno-          benzène-sulfonyle,    de manière à former, par  élimination     d'hal,ogénure    d'hydrogène, le     2-          (para-hal!ogéno-benzène-sulfamido)-thiazal,     puis en te que l'on traite ce dernier corps  avec de     l'ammoniaque    pour remplacer l'halo  gène par un groupe     amino,

      de façon à -obte  nir le     2-(para-amino-benzène-sulfamido)-          thiazol.       L'exemple suivant     montre    -comment le  procédé selon l'invention peut être mis en  pratique:  7,7 gr de chlorure de     para-b:romo-benzène-          sulfonylesont    ajoutés lentement à     une,solu-          tion    de     â    gr .de     2-amino-thiazol        dans.    15     em3     de     pyridine    anhydre.

   On. chauffe quelque  temps le mélange au     bain-marie,    on     1e        laisse     reposer 1 heure, puis on le verse dans 200     cm3          d'-eau.    Le     précipité    -est rassemblé, puis     redis-          sous    dans 20 cm' d'une     solution    chaude de       'soude        caustique    2N. Par     refroidissement,    le  Gel de     ,sodium    se     isépare    sous forme cristal  line. Il est filtré- et     rediss,ousdans    l'eau.

    Après traitement nu noir décolorant,     #la    solu  tion est acidifiée par de d'acide acétique, ce  qui fait précipiter le     2-(para-b.romo-benzène-          sulfamid,o)-thiazol    sous forme de     paillettes     fondant à 211   C.  



  11,4 gr du dérivé bromé sont chauffés  5 h en tube scellé à 110-120   C avec 20 cm'  d'une solution     aqueuse-d'ammoniaque,    de den-           sité        0,8 & U    additionnés de 0,1 gr de chlorure  cuivreux.  



  On fait     bouillir    la     solution    obtenue avec  un peu de charbon décolorant et filtre. Pen  dant qu'elle     est    encore chaude, la solution est  additionnée d'assez d'acide acétique pour     re-          dissoudre    le précipité d'abord formé. Par re  froidissement, le     2-(para-amino-benzène-          sulfamido)-thiazol    cristallise en prismes  plats fondant à 195-196   C.



  Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol. The present invention relates to a process .de preparation of 2- (para-amino-benzene-sulfamido) -thi.a7, ol, having the formula:
EMI0001.0004
    This compound melts at 196-197 C. It is sparingly soluble in water, it exhibits remarkable bactericidal properties and is capable of application & therapy.



  The process according to the invention is characterized in that 2-amino-thiazol is reacted with a para-ha logenobenzene-sulfonyl halide, so as to form, by elimination of hal, hydrogen, 2- (para-hal! ogeno-benzene-sulfamido) -thiazal, then by treating the latter body with ammonia to replace the halogen with an amino group,

      so as to -obte ne 2- (para-amino-benzene-sulfamido) - thiazol. The following example shows how the process according to the invention can be put into practice: 7.7 g of para-b: romo-benzene-sulfonyl chloride are slowly added to a solution of α 2- amino-thiazol in. 15 em3 of anhydrous pyridine.

   We. Heat the mixture for some time in a water bath, let it stand for 1 hour, then pour it into 200 cm3 of water. The precipitate is collected and then redissolved in 20 cm 3 of hot 2N sodium hydroxide solution. On cooling, the sodium gel is separated in crystal line form. It is filtered and redissolved, or in water.

    After a bleaching black treatment, #the solution is acidified with acetic acid, which precipitates the 2- (para-b.romo-benzene-sulfamid, o) -thiazol in the form of flakes, melting at 211 C.



  11.4 g of the brominated derivative are heated for 5 h in a sealed tube at 110-120 C with 20 cm 'of an aqueous-ammonia solution, density 0.8%, added with 0.1 g of chloride. copper.



  The solution obtained is boiled with a little decolorizing charcoal and filtered. While still hot, enough acetic acid is added to the solution to re-dissolve the precipitate first formed. On cooling, 2- (para-amino-benzenesulfamido) -thiazol crystallizes in flat prisms melting at 195-196 C.

Claims (1)

REVENDICATION Procédé de préparation du 2-(para-amino- benzène-sulfamido)-tlriazol, caractérisé en ce que l'on fait réagir du 2-amino-thiazol avec un halogénure de pa: CLAIM Process for the preparation of 2- (para-amino-benzene-sulfamido) -tlriazol, characterized in that 2-amino-thiazol is reacted with a pa halide: ra-halogéno-benzène- sulfonyle, de manière à former, par élimina tion d'halogénure d'hydrogène, le 2-(para- halogéno-benzène-sulfamido)-thiazol, puis en ce que l'on traite ce dernier corps avec de l'ammoniaque pour remplacer 1'llalogéne par un groupe amine, de façon à obtenir le 2-(para-amino-benzène-sulfamido)-thiazol. Ce dernier composé fond à 196-197 C; il est peu soluble dans l'eau; ra-halo-benzene-sulfonyl, so as to form, by elimination of hydrogen halide, 2- (para-halo-benzene-sulfamido) -thiazol, then in that the latter body is treated with ammonia to replace the halogen by an amine group, so as to obtain 2- (para-amino-benzene-sulfamido) -thiazol. The latter compound melts at 196-197 C; it is poorly soluble in water; il présente des pro priétés bactéricides marquantes et est suscep tible d'applications thérapeutiques. SOUS-REVENDICATION Procédé selon la revendication, caractérisé. it exhibits striking bactericidal properties and is susceptible to therapeutic applications. SUB-CLAIM Method according to claim, characterized. en ce que l'on fait réagir du 2-amino-thiazol avec du chlorure de para-bromo-benzène- sulfonyle, puis en ce que l'on traite à chaud le produit obtenu avec une solution aqueuse d'ammoniaque, en présence de chlorure cui vreux. in that 2-amino-thiazol is reacted with para-bromo-benzenesulfonyl chloride, and then in that the product obtained is treated under heat with an aqueous solution of ammonia, in the presence of copper chloride.
CH218231D 1938-06-03 1939-06-01 Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol. CH218231A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB218231X 1938-06-03

Publications (1)

Publication Number Publication Date
CH218231A true CH218231A (en) 1941-11-30

Family

ID=10169398

Family Applications (1)

Application Number Title Priority Date Filing Date
CH218231D CH218231A (en) 1938-06-03 1939-06-01 Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol.

Country Status (1)

Country Link
CH (1) CH218231A (en)

Similar Documents

Publication Publication Date Title
US2149279A (en) Derivatives of pyrazine carboxylic acid and processes for their production
CN114213260B (en) Preparation method of prionamine iodide
US2085009A (en) Di-halogen substituted alpha-(p-hydroxyphenyl)-alpha-amino-acetic acid, hydrohalides of the same, and processes for their production
DE608434C (en) Process for the preparation of condensation products from 2,3-oxynaphthoic acid and anthranilic acid amide or its substitution products
DE1543893B2 (en) Process for the preparation of N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide
CH220343A (en) Process for the preparation of 2- (para-amino-benzenesulfamido) -thiazol.
CH220674A (en) Process for the preparation of 2- (para-amino-benzene-sulfamido) -4-methyl-thiazol.
AT206578B (en)
Adams et al. Quinone Imides. XXVI. Adducts of p-Quinonebis-(dimethylaminosulfonimides) and their Hydrolysis Products
CH216545A (en) Process for the preparation of 2- (para-amino-benzene-sulfamido) -thiazol.
US268543A (en) Cheistiast kudolph
CH231026A (en) A process for preparing para-aminobenzenesulfamido-2-n-heptyl-5-thiodiazol-1,3,4.
CH275969A (en) A process for preparing a substituted sulfanilamido-quinoxaline.
CH365077A (en) Process for the preparation of novel isothiazole derivatives
CH525187A (en) N-(2-diethylaminoethyl)-2-methoxy-4-substd 5-chlorobenzamides - - from 2-methoxy-4-substd-5-chlorobenzoic acid 2-(diethylamino)-ethyl
CH220137A (en) Process for the preparation of 2- (para-amino-benzene-sulfamido) -4-methyl-thiazol.
CH105359A (en) Process for preparing diethylchloroacetamide.
CH294510A (en) Process for preparing hexamethylene-1,6-trimethylammonium bitartrate.
CH178537A (en) Process for the preparation of a condensation product of 2,3-oxynaphthoic acid with anthranilic acid amide.
CH414668A (en) Process for the preparation of N- (2,3-dimethylphenyl) -anthranilic acid
CH267812A (en) Process for the production of a new derivative of benzenesulfonamide.
CH294177A (en) Process for the preparation of a new derivative of pyridine.
CH336832A (en) Process for the preparation of substituted heterocyclic sulfonamides
BE527500A (en)
Schryver LVIII.—Researches on camphoric acid