CH207309A - Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. - Google Patents

Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.

Info

Publication number
CH207309A
CH207309A CH207309DA CH207309A CH 207309 A CH207309 A CH 207309A CH 207309D A CH207309D A CH 207309DA CH 207309 A CH207309 A CH 207309A
Authority
CH
Switzerland
Prior art keywords
para
pyridine
amino
hydrolysis
benzenesulfamido
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 CH207309A publication Critical patent/CH207309A/en

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Classifications

    • 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

Landscapes

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

Description

  

  Procédé de préparation de. la     2-(para-amino-benzène-snlfamido)-pyridine.       La présente invention a pour objet un  procédé de préparation de la     2-(para-amino-          benzène-sulfamido)-pyridine,    ayant pour for  mule  
EMI0001.0004     
    Ce composé fond à 190   C; il est peu  soluble à froid dans l'eau, l'acétone, l'alcool;  il présente des propriétés bactéricides mar  quantes et il est susceptible d'applications  thérapeutiques.  



  Le procédé selon l'invention est caracté  risé en ce que l'on fait réagir de la     2-halogéno-          pyridine    avec une     para-acyle-amino-benzène-          sulfamide,    de manière à former, en éliminant  de l'halogénure d'hydrogène, de la     2-(para-          acyle-amino-benzéne-sulfamido)-pyridine,    puis  en ce que l'on soumet ce dernier corps à une  hydrolyse pour en éliminer le groupe acyle  et obtenir la     2-(para-amino-benzèn        e-salfamido)-          pyridine.       Voici, à titre d'exemple, comment ce pro  cédé peut être exécuté:

    Un mélange de 21,4 g de     p-acétylamino-          benzène-sulfamide,    de 13 g de carbonate de  potasse anhydre, de 1 g de poudre de cuivre  et de 15,8 g de     2-bromo-pyridine    est chauffé  à 200-240   pendant 1 heure. Le produit  fondu est dissous dans l'eau bouillante et  filtré. En acidifiant avec l'acide acétique, on  obtient la     2-(p    -     acétylamino    -benzène-     sulfa-          mido)-pyridine    (point de fusion 224  ), à partir  de laquelle on prépare la     2-(p-amino-sulfa-          mido)-pyridine,    par hydrolyse alcaline.

   Cette  dernière peut être conduite comme indiqué  au brevet principal.



  Process for the preparation of. 2- (para-amino-benzene-snlfamido) -pyridine. The present invention relates to a process for the preparation of 2- (para-amino-benzene-sulfamido) -pyridine, having the formula
EMI0001.0004
    This compound melts at 190 C; it is poorly soluble in cold water, acetone, alcohol; it has remarkable bactericidal properties and is capable of therapeutic applications.



  The process according to the invention is characterized in that 2-halogenopyridine is reacted with a para-acyl-amino-benzenesulfamide, so as to form, by removing hydrogen halide , 2- (para-acyl-amino-benzen-sulfamido) -pyridine, then in that the latter body is subjected to hydrolysis to remove the acyl group and obtain 2- (para-amino-benzen e-salfamido) - pyridine. Here is, as an example, how this process can be performed:

    A mixture of 21.4 g of p-acetylamino-benzene-sulfonamide, 13 g of anhydrous potassium carbonate, 1 g of copper powder and 15.8 g of 2-bromo-pyridine is heated to 200-240 for 1 hour. The molten product is dissolved in boiling water and filtered. Acidification with acetic acid gives 2- (p-acetylamino -benzene-sulfamido) -pyridine (melting point 224), from which 2- (p-amino-sulfamido) is prepared. ) -pyridine, by alkaline hydrolysis.

   The latter can be carried out as indicated in the main patent.

Claims (1)

REVENDICATION Procédé de préparation de la 2-(para-amino- benzène-sulfamido)-pyridine, caractérisé en ce que l'on fait réagir de la 2-halogéno-pyridine avec une para-acyle-amino-benzène-sulfamide, de manière à former, en éliminant de l'halo- génure d'hydrogène, de 1a 2-(para-acyle-amino- benzène-sulfamido)-pyridine, puis en ce que l'on soumet ce dernier corps à une hydrolyse pour en éliminer le groupe acyle et obtenir la 2-(para-amino-benzène-sulfamido)-pyridine. Cette dernière fond à 190 C ; CLAIM Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine, characterized in that 2-halo-pyridine is reacted with a para-acyl-amino-benzenesulfonamide, so to form, by removing hydrogen halide, 2- (para-acyl-amino-benzene-sulfamido) -pyridine, and then subjecting the latter body to hydrolysis to remove therefrom the acyl group and obtain 2- (para-amino-benzenesulfamido) -pyridine. The latter melts at 190 C; elle est peu soluble à froid dans l'eau, l'acétone, l'alcool: elle présente des propriétés bactéricides mar quantes et elle est susceptible d'applications thérapeutiques. SOUS-REVENDICATIONS 1 Procédé selon la revendication, caractéri4é en ce que l'on fait réagir de la 2-bromo- pyridine avec de la para -acétyl-amino- benzéne-sulfamide, puis en ce que l'on soumet le produit obtenu à une hydrolyse. 2 Procédé selon "la revendication, caractérisé en ce que l'on effectue l'hydrolyse en milieu alcalin. it is not very soluble when cold in water, acetone or alcohol: it has remarkable bactericidal properties and it is susceptible of therapeutic applications. SUB-CLAIMS 1 Process according to claim, characterized in that 2-bromopyridine is reacted with para -acetyl-aminobenzene-sulfonylurea, then in that the product obtained is subjected to hydrolysis. 2 A method according to "claim, characterized in that the hydrolysis is carried out in an alkaline medium. 3 Procédé selon la revendication, caractérisé en ce que l'on chauffe un mélange de 2-bromo-pyridine, de para- acétyl-amino- benzène-sulfamide, de carbonate de potas sium anhydre et de poudre de cuivre, en ce que l'on dissout le produit obtenu dans de l'eau et on le soumet à une hydrolyse alcaline. 3 A method according to claim, characterized in that a mixture of 2-bromo-pyridine, para-acetyl-amino-benzenesulfonylurea, anhydrous potassium carbonate and copper powder is heated, in that the the product obtained is dissolved in water and subjected to alkaline hydrolysis.
CH207309D 1937-07-14 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. CH207309A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH205678T 1937-07-14
GB207309X 1938-05-12

Publications (1)

Publication Number Publication Date
CH207309A true CH207309A (en) 1939-10-15

Family

ID=25724206

Family Applications (1)

Application Number Title Priority Date Filing Date
CH207309D CH207309A (en) 1937-07-14 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.

Country Status (1)

Country Link
CH (1) CH207309A (en)

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