CH205679A - Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. - Google Patents

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

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Publication number
CH205679A
CH205679A CH205679DA CH205679A CH 205679 A CH205679 A CH 205679A CH 205679D A CH205679D A CH 205679DA CH 205679 A CH205679 A CH 205679A
Authority
CH
Switzerland
Prior art keywords
para
pyridine
amino
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 CH205679A publication Critical patent/CH205679A/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

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

Description

  

  Procédé de préparation de la     2-(para-amino-benzène-sulfamido)-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 so  luble 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 carac  térisé en ce que l'on fait réagir de la     2-amino-          pyridine    avec un halogénure de     benzène-          sulfonyle,    substitué en para par un reste  susceptible de donner par réduction le groupe       -N112,    de manière à former, en     éliminant    de  l'halogénure d'hydrogène, un     dérivé    de la       2-benzène-sulfamido-pyridine    ayant ledit  reste en position para, puis en ce que l'on    effectue la réduction de manière .à obtenir la       2-(para-amino-benzène    -     sulfamido)

          -pyridine.     



  On peut par exemple faire réagir avec de  la     2-amino-pyridine    soit du chlorure de       para-nitro-benzène-sulfonyle,    soit du chlorure  de para -     diéthylamino    -     azobenzène-parasul-          fonyle,    puis réduire le composé obtenu.  



  Voici deux exemples de mise en     aeuvre    du  procédé de l'invention:  <I>Exemple 1:</I>  A une solution de 4,7 g de     2-amino-pyri-          dine    dans 10     em3    de     pyridine    sèche on ajoute,  en refroidissant, 12 g de chlorure de     p-nitro-          benzène-sulfonyle.    Une     réaction    énergique  se produit; quand celle-ci est terminée, le mé  lange est dilué à l'eau (200 cm') et le préci  pité de     2-(p-nitro-benzène-sulfamido)-pyri-          dine    est     recueilli.    Point de fusion: 185   C.  



  Le composé nitré     @(1,4    g) est dissous dans  environ 5 cm'     d'une    solution de soude 2N  et la suspension du sel de sodium formée au      repos est ajoutée à     '-)0             C à une pâte     d'liydro-          xyde    ferreux obtenue à partir de 10 g de sul  fate ferreux (hydraté) dans 30 cm' d'eau et  3 g de soude dans 5 cm' d'eau. Après repos  (une heure), le mélange est filtré de l'hy  droxyde ferrique et le filtrat acidifié à l'acide  acétique. La     2-(p-amino-benzène-sulfamido)-          pyridine    obtenue fond à 190   C.  



       Exemple.   <I>2:</I>  7 g de chlorure de     p-diéthylamino-azo-          benzène-p'-sulfonyle    (préparé par l'action du       pentachlorure    de phosphore sur le     p-diéthyl-          amino-azo-benzène-p'-sulfonate    de sodium)  sont ajoutés à 1,9 g de     2-amino-pyridine    dis  sous dans 20 cm' de     pyridine.    Après que la  réaction est terminée, on ajoute de l'eau. La       2-(p-diéthyl-amino-azobenzène-p'-sulfamido)-          pyridine    précipitée est filtrée, lavée à l'eau  et dissoute dans 5 parties d'une solution de  soude 2N.

   La solution est chauffée à 30 à  40   C et on ajoute peu à peu de     l'hydro-          sulfite    de sodium solide jusqu'à ce que la co  loration rouge de la solution disparaisse. On  ajoute alors de l'acide acétique jusqu'à ce que  la, solution soit légèrement acide; par concen  tration la     2-(p-amino-benzène-sulfamido)-          pyridine    se sépare et on la purifie par     re-          cristallisation    à l'alcool. Point de fusion:  <B>190</B>   C.



  Process for the preparation of 2- (para-amino-benzenesulfamido) -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 not very soluble when cold in water, acetone or alcohol; it has remarkable bactericidal properties and is capable of therapeutic applications.



  The process according to the invention is characterized in that 2-amino-pyridine is reacted with a benzene-sulfonyl halide, substituted in para by a residue capable of giving by reduction the group -N112, so in forming, by removing hydrogen halide, a derivative of 2-benzene-sulfamido-pyridine having said residue in the para position, then in that the reduction is carried out so as to obtain the 2- ( para-amino-benzene - sulfamido)

          -pyridine.



  For example, it is possible to react with 2-amino-pyridine either para-nitro-benzene-sulfonyl chloride or para-diethylamino-azobenzene-parasulfonyl chloride, then reduce the compound obtained.



  Here are two examples of implementation of the process of the invention: <I> Example 1: </I> To a solution of 4.7 g of 2-amino-pyridine in 10 em3 of dry pyridine is added, in cooling, 12 g of p-nitro-benzene-sulfonyl chloride. A vigorous reaction occurs; when this is finished, the mixture is diluted with water (200 cm 3) and the precipitate of 2- (p-nitro-benzene-sulfamido) -pyridine is collected. Melting point: 185 C.



  The nitro compound (1.4 g) is dissolved in about 5 cm 3 of a 2N sodium hydroxide solution and the suspension of the sodium salt formed on standing is added at '-) 0 C to a paste of hydroxide. ferrous obtained from 10 g of ferrous sulfate (hydrated) in 30 cm 3 of water and 3 g of soda in 5 cm of water. After standing (one hour), the mixture is filtered with ferric hydroxide and the filtrate acidified with acetic acid. The 2- (p-amino-benzene-sulfamido) - pyridine obtained melts at 190 C.



       Example. <I> 2: </I> 7 g of p-diethylamino-azobenzene-p'-sulfonyl chloride (prepared by the action of phosphorus pentachloride on p-diethyl-amino-azo-benzene-p ' -sodium sulfonate) are added to 1.9 g of 2-amino-pyridine dissolved in 20 cm 'of pyridine. After the reaction is complete, water is added. The 2- (p-diethyl-amino-azobenzene-p'-sulfamido) - pyridine which precipitates is filtered off, washed with water and dissolved in 5 parts of a 2N sodium hydroxide solution.

   The solution is heated to 30 to 40 ° C. and solid sodium hydrosulphite is gradually added until the red color of the solution disappears. Acetic acid is then added until the solution is slightly acidic; on concentration the 2- (p-amino-benzenesulfamido) -pyridine separates and is purified by recrystallization with alcohol. Melting point: <B> 190 </B> C.

Claims (1)

REVENDICATION Procédé de préparation de la 2-(para- amino-benzène-sulfamido)-pyridine, caracté risé en ce que l'on fait. réagir de la 2-amino- pyridine avec un halogénure de benzène- sulfonyle, substitué en para par un reste sus ceptible de donner par réduction le groupe -NH@, de manière à. CLAIM Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine, characterized in that it is done. reacting 2-amino-pyridine with a benzene-sulfonyl halide, substituted in para by a residue capable of giving by reduction the group -NH @, so as to. former, en éliminant de l'halogénure d'hydrogène, un dérivé de la 2- benzène-sulfamido-pyridine ayant ledit reste en position para, puis en ce que l'on effectue la réduction de manière à obtenir de la 2 (para - amino - benzène - sulfamido) -pyridine. Cette dernière fond à 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 suceptible d'applications thérapeutiques. to form, by eliminating hydrogen halide, a 2-benzene-sulfamido-pyridine derivative having said residue in the para position, then in that the reduction is carried out so as to obtain 2 (para - amino - benzene - sulfamido) -pyridine. The latter melts at 190 C; it is poorly soluble when cold in water, acetone and alcohol; it has remarkable bactericidal properties and is susceptible to therapeutic applications. SOUS-REVE-.\TDICATIONS 1 Procédé selon la revendication, caractérisé en ce que l'on fait réagir de la 2-amino- pyridine avec du chlorure de para-nitro- benzène-sulfonyie, de manière à obtenir de la 2-(para-nitro-benzène-sulfamido)-pyri- dine, puis en ce que l'on réduit cette der nière. SUB-DREAM -. \ TDICATIONS 1 Process according to claim, characterized in that 2-amino-pyridine is reacted with para-nitro-benzene-sulfonyl chloride, so as to obtain 2- ( para-nitro-benzene-sulfamido) -pyri- dine, then in that the latter is reduced. 2 Procédé selon la revendication, caractérisé en ce que l'on fait réagir de la. 2-amino- py ridine avec du chlorure de paradiéthyl- amiiio-azobenzène-para'-sulfonyle, de ma nière<B>à</B> obtenir de la ?-(para-diéthyl-amino- azoben7ène-para'-sulfamido)-pyridine, puis en ce que l'on réduit cette dernière. 3 Procédé selon la revendication et la sous- revendication 1, caractérisé en ce que l'on effectue ladite réduction avec de l'hy droxyde ferreux. 2 Method according to claim, characterized in that one reacts the. 2-amino-py ridine with paradiethyl-amiiio-azobenzene-para'-sulfonyl chloride, so as <B> to </B> obtain? - (para-diethyl-amino-azoben7ene-para'-sulfamido ) -pyridine, then in that the latter is reduced. 3 A method according to claim and sub-claim 1, characterized in that said reduction is carried out with ferrous hydroxide. 4 Procédé selon la revendication et la sous- revendication 2. caractérisé en ce que l'on effectue ladite réduction avec de l'hydro- sulfite de sodium. 4 A method according to claim and sub-claim 2. characterized in that said reduction is carried out with sodium hydrosulphite.
CH205679D 1937-11-29 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. CH205679A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB205679X 1937-11-29

Publications (1)

Publication Number Publication Date
CH205679A true CH205679A (en) 1939-06-30

Family

ID=10148056

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205679D CH205679A (en) 1937-11-29 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.

Country Status (1)

Country Link
CH (1) CH205679A (en)

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