CH201765A - Process for the preparation of parabenzylaminobenzenesulfamide. - Google Patents

Process for the preparation of parabenzylaminobenzenesulfamide.

Info

Publication number
CH201765A
CH201765A CH201765DA CH201765A CH 201765 A CH201765 A CH 201765A CH 201765D A CH201765D A CH 201765DA CH 201765 A CH201765 A CH 201765A
Authority
CH
Switzerland
Prior art keywords
preparation
para
acetylbenzylaniline
ammonia
parabenzylaminobenzenesulfamide
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 CH201765A publication Critical patent/CH201765A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides 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
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Procédé de préparation de la     parabenzylaminobenzènesulfamide.       On sait que les.     dérivés    de la.     p-aminoben-          zènesulfamide,    substitués sur le groupe       amino    par un reste     aralcoyl,    ont des proprié  tés bactéricides, en     particulier    sur les strepto  coques; parmi ces     dérivés    on peut     citer    la       para-benzylaminobenzènesulf    amide.  



  On a décrit dans les brevets suisses  nos 192699 et 192700 deux procédés de prépa  ration de la     para-benzylaminobenzènesulfa-          mide.     



  Poursuivant ses recherches, la demande-         resse    a trouvé qu'on peut facilement préparer  la     para-benzylaminobenzènesulfamide,    ainsi  que d'autres     p-aminobenzènesulfamides        N-          aralkylées    (par exemple la     para-phénylpro-          pylaminobenzènesulfamide)    en faisant réa  gir sur     l'acétylbenzylaniline    ou ses homo  logues     correspondants,    la     chlorhydrine    sulfu  rique et en     traitant    le     sulfoehlorure    formé par  l'ammoniaque.

   La formule ci-après donne une       représentation        schématique    des réactions de       cette    préparation:  
EMI0001.0028     
    La présente invention a donc pour objet  un     procédé    de préparation de la     para-benzyl-          aminobenzènesulfamide.       Ce procédé     -est    caractérisé en ce que l'on  fait réagir de     l'acétylbenzylaniline    avec de  la     chlorhydrine    sulfurique, de manière à for-      mer le     para-sulfochlorure    correspondant,  puis en ce que l'on traite ce dernier par l'am  moniaque et l'eau.  



  Voici, à titre d'exemple, comment le pro  cédé de l'invention peut être réalisé en pra  tique:  On ajoute à 145 gr de     chlorhydrine    sul  furique, en heure, en agitant et en main  tenant la     température    au-dessus de 20   C.  55 gr     d'acétylbenzylaniline.    On porte alors  la température à 65   et on maintient le  chauffage et l'agitation pendant ? h. On re  froidit et l'on coule peu à peu sur 400     gr    de       glace    pilée. On reprend par ?00 cm' de ben  zène qui dissout le     sulfochlorRZre    brut préci  pité.

   On coule, en refroidissant et en agitant  la solution décantée dans 200     emd    d'ammonia  que à. 22       Bé.    On filtre le précipité solide       après    quelques minutes de repos et on le     re-          cristallise    dans l'alcool ou l'acétone à. 50 . Le  produit fond à 175  ,     comme    celui obtenu  par les procédés des brevets suisses     nos    193699  et     19\3700.  



  Process for the preparation of parabenzylaminobenzenesulfamide. We know that the. derived from the. p-aminobenzenesulfamide, substituted on the amino group by an aralkyl residue, have bactericidal properties, in particular on streptococci; among these derivatives, mention may be made of para-benzylaminobenzenesulf amide.



  Two processes for the preparation of para-benzylaminobenzenesulfamide have been described in Swiss Patents Nos. 192699 and 192700.



  Continuing her research, the applicant has found that para-benzylaminobenzenesulfamide, as well as other N-aralkylated p-aminobenzenesulfonamides (for example para-phenylpropylaminobenzenesulfamide) can easily be prepared by reacting on acetylbenzylaniline. or its corresponding counterparts, sulfuric chlorohydrin and by treating the sulfohloride formed by ammonia.

   The formula below gives a schematic representation of the reactions of this preparation:
EMI0001.0028
    A subject of the present invention is therefore a process for the preparation of para-benzylaminobenzenesulfamide. This process -is characterized in that one reacts acetylbenzylaniline with sulfuric chlorohydrin, so as to form the corresponding para-sulfochloride, then in that the latter is treated with ammonia. and water.



  Here is, by way of example, how the process of the invention can be carried out in practice: 145 g of sulfuric chlorohydrin are added to 145 g, in the hour, while stirring and keeping the temperature above 20 ° C. 55 gr of acetylbenzylaniline. The temperature is then brought to 65 and the heating and stirring are maintained for? h. Cool down again and gradually pour over 400 g of crushed ice. It is taken up in 00 cm 'of ben zene which dissolves the abovementioned crude sulfochlorRZre.

   Poured, cooling and stirring the solution decanted in 200 emd of ammonia as. 22 Bé. The solid precipitate is filtered off after standing for a few minutes and recrystallized from alcohol or acetone. 50. The product melts at 175, like that obtained by the methods of Swiss Patent Nos. 193699 and 19 \ 3700.

Claims (1)

P,EVENDICATION Procédé de préparation de la para-benzyl - aminobenzènesulfamide, caractérisé en ce que l'on fait réagir de l'acétylbenzylaniline avec de la. chlorhydrine sulfurique. de manière à former le para-sulfochlorure correspondant, puis en ce que l'on traite ce dernier par l'am- monia.que et l'eau. P, EVENDICATION Process for the preparation of para-benzyl - aminobenzenesulfamide, characterized in that acetylbenzylaniline is reacted with. sulfuric chlorohydrin. so as to form the corresponding para-sulfochloride, then in that the latter is treated with ammonia and water. SOUS-REVENDICATIOE S 1 Procédé selon la revendication, caractérisé en ce que l'on conduit la réaction entre l'acétylbenzylaniline et la chlorhydrine sulfurique, au-dessus de 20 C. Procédé selon la. revendication, caractérisé en ce que l'on traite le pa.ra-sulfochlorure avec de l'ammoniaque à 22 Bé. SUB-CLAIM S 1 A method according to claim, characterized in that the reaction is carried out between acetylbenzylaniline and sulfuric chlorohydrin, above 20 C. Method according to. claim, characterized in that the pa.ra-sulfochloride is treated with 22 Bé ammonia.
CH201765D 1937-03-19 1938-03-17 Process for the preparation of parabenzylaminobenzenesulfamide. CH201765A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB201765X 1937-03-19

Publications (1)

Publication Number Publication Date
CH201765A true CH201765A (en) 1938-12-15

Family

ID=10141651

Family Applications (1)

Application Number Title Priority Date Filing Date
CH201765D CH201765A (en) 1937-03-19 1938-03-17 Process for the preparation of parabenzylaminobenzenesulfamide.

Country Status (1)

Country Link
CH (1) CH201765A (en)

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