CH205680A - 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
CH205680A
CH205680A CH205680DA CH205680A CH 205680 A CH205680 A CH 205680A CH 205680D A CH205680D A CH 205680DA CH 205680 A CH205680 A CH 205680A
Authority
CH
Switzerland
Prior art keywords
para
pyridine
amino
benzenesulfamido
preparation
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 CH205680A publication Critical patent/CH205680A/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)
  • Pyridine 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:  
EMI0001.0005     
    Ce composé fond à<B>190'</B> 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     para-halogéno-          benzène-sulfonyle,    de manière à former, en  éliminant de l'halogénure d'hydrogène, de la       2a(para-halogéno    - benzène -     sulfamido)    -     pyri-          dine,    puis en ce que l'on traite ce dernier  corps avec de l'ammoniaque de façon à rem  placer l'halogène par un groupe     amino    pour    obtenir la     2-(para-amino-benzène-sulfamido)-          pyridine.     



  Voici, à titre d'exemple, comment ce pro  cédé     peut,être    exécuté:  16,5 g de chlorure de     p-chloro-benzène-          sulfonyle    sont ajoutés à une solution de 7 g  de     2-amino-pyridine    dans 20 cm' de     pyridine.     Après chauffage à<B>90'</B> C pendant 15 minutes,  on ajoute de l'eau et la     2-(p-chlorobenzène-          sulfamido)-pyridine    précipitée est séparée,  lavée et séchée. Point de fusion: 186   C.

    Celle-ci est alors chauffée en vase clos avec  quatre fois son poids d'une solution aqueuse  concentrée d'ammoniaque, en présence d'envi  ron     1/_o    de son poids de chlorure cuivreux,  pendant 18 heures, à 150-175   C.  



  L'excès d'ammoniaque est éliminé et, par  dilution avec de l'eau, on obtient la     2-(p-          amino-benzène-sulfamido)-pyridine    qui peut  être purifiée par cristallisation à l'eau. 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-benzenesulfamido) -pyridine, having the following formula:
EMI0001.0005
    This compound melts at <B> 190 '</B> 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 para-halogenobenzene-sulfonyl halide, so as to form, by removing hydrogen halide , 2a (para-halo - benzene - sulfamido) - pyridine, then in that the latter body is treated with ammonia so as to replace the halogen with an amino group to obtain the 2 - (para-amino-benzene-sulfamido) - pyridine.



  Here is, by way of example, how this process can be carried out: 16.5 g of p-chloro-benzene-sulfonyl chloride are added to a solution of 7 g of 2-amino-pyridine in 20 cm 3 of pyridine. After heating at <B> 90 ° </B> C for 15 minutes, water is added and the precipitated 2- (p-chlorobenzenesulfamido) -pyridine is separated, washed and dried. Melting point: 186 C.

    This is then heated in a closed vessel with four times its weight of a concentrated aqueous ammonia solution, in the presence of about 1 / _o of its weight of cuprous chloride, for 18 hours, at 150-175 C.



  The excess ammonia is removed and, on dilution with water, 2- (p-amino-benzene-sulfamido) -pyridine is obtained which can be purified by crystallization from water. Melting point: <B> 190 </B> C.

Claims (1)

REVENDICATION Procédé de préparation de la \2-ipara.- amino-benzène-sulfamido)-pyridine, caracté risé en ce que l'on fait réagir de la 2-amino- pyridine avec un halogénure de para -ha,logéno- benzène-sulfonyle, de manière à former, en éliminant de l'halogénure d'hydrogène, de la 2-(para - halogéno - benzène - sulfamido)-py ri- dine, CLAIM Process for the preparation of \ 2-ipara.- amino-benzenesulfamido) -pyridine, characterized in that 2-aminopyridine is reacted with a para -ha halide, logenobenzene- sulfonyl, so as to form, by eliminating hydrogen halide, 2- (para - halo - benzene - sulfamido) -py ri- dine, puis en ce que l'on traite ce dernier corps avec de l'ammoniaque de façon à rem placer l'halogène par un groupe amino pour obtenir la 2-.(para-amino-benzène-sulfamido)- pyridine. Cette dernière fond à<B>190'</B> C; elle est peu soluble à froid dans l'eau, l'acétone, l'alcool; elle présente des propriétés bactéri- cides marquantes et elle est susceptible d'ap plications thérapeutiques. then in that the latter body is treated with ammonia so as to replace the halogen with an amino group to obtain 2 -. (para-amino-benzene-sulfamido) - pyridine. The latter melts at <B> 190 '</B> C; it is poorly soluble when cold in water, acetone and alcohol; it exhibits remarkable bactericidal properties and is capable of therapeutic applications. SOUS-REVENDICATION: Procédé selon la revendication, caractérisé en ce que l'on fait réagir de la 2-amino- pyridine avec du chlorure de para-chloro- benzène-sulfonyle, puis en ce que l'on traite à chaud le produit obtenu avec une solution aqueuse d'ammoniaque, en présence de chlo rure cuivreux. SUB-CLAIM: Process according to claim, characterized in that 2-amino-pyridine is reacted with para-chlorobenzene-sulfonyl chloride, then in that the product obtained is heat treated. with an aqueous solution of ammonia, in the presence of cuprous chloride.
CH205680D 1938-05-12 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. CH205680A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB205680X 1938-05-12

Publications (1)

Publication Number Publication Date
CH205680A true CH205680A (en) 1939-06-30

Family

ID=10148057

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205680D CH205680A (en) 1938-05-12 1938-11-15 Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine.

Country Status (1)

Country Link
CH (1) CH205680A (en)

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