CH242488A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents

Description

  

      Yerfaliren for the manufacture of a new benzenesulfonamide derivative. The subject of the present patent is a process for the preparation of a new Benzo @ Isulfonamidderivates, which is characterized by;

       that a 2-benzenesulfonainidoquinogaline, which has a substituent in the p-position which can be converted into the amino group by hydrolysis, is treated with a hydrolyzing agent.



  The 2 - (p-amino-benzenesulfonamido) -chinogali.n obtained in this way is a crystalline powder of F. 244-245 (with decomposition). The new compound is to be used as a drug and as an intermediate product.



  The 2-benzenesulfonamido-ehinogalin, which in the p-position to the sulfonamide group contains a substituent which can be converted into the amino group by hydrolysis, can be obtained in various ways.

   The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with quinogaline compounds which contain a group in the 2-position which is able to form a 2-benzenesulfonamidoquinogaline with the benzenesulfonic acid derivative, such as mixes 2, is particularly suitable -Amino-quinogaline. Corresponding sulfonamides of the formula R can also be used.

       S02NHY, in which Y denotes a radical which is split off in the subsequent reaction, with 2-haloquinogalines. Other manufacturing methods familiar to the specialist can also be used.



  <I> Example: </I> 145 parts of 2-amino-cMnogalin are dissolved in 750 parts of dry pyridine on a water bath. It is cooled to about 20 and, with further cooling and stirring, 265.5 parts of p-carbethogyamino-benzenesulphonyl chloride are slowly introduced.

   After the end of the introduction, the mixture is heated for 1 hour on the boiling water bath and the excess pyridine is distilled off in vacuo on the water bath. Water and then hydrochloric acid are added to the residue until the Congo acidic reaction occurs, whereupon the formed 2- (p-carbethogyamino-benzenesulfonamido) -quinogaln is deposited in crystallized form.

    It is filtered off with suction, washed with water and recrystallized from dilute alcohol with the addition of animal charcoal. F. 2l2 = 214.



  186 parts of 2- (p-Carbäthögyamino-benzene-sulfonamido) -quinogalin are in. 800 parts, 2N sodium hydroxide solution for 1 hour at 95 he warms. It is then stirred with animal charcoal, filtered and 2- (p-Am.no-benzenesulfonamido) -quinogaline is precipitated with hydrochloric acid. You suction off, wash with water and dry. F. 244-245 (with decomposition). You can recrystallize from a lot of about 80% alcohol. .



  It is possible to carry out the hydrolysis with other alkaline agents, for example Brdalkalihydrogyden, such as calcium hydrogen, or with acidic agents, e.g. B: hydrochloric acid, in the presence of water or organic solvents such as alcohol.



  The p-amino-benzenesulfonamide derivative formed can also be used in the form of its salts, e.g. B. sodium or calcium, iso lieren.

 

Claims (1)

PATENT CLAIM: Process for the production of a new benzenesulfonamide derivative, characterized in that a 2-benzenesulfonamidoquinogaline, which has a substituent which can be converted into the amino group by hydrolysis, is treated with an ilydrolysing agent. The 2 - (p - amino - benzenesulfonamido) quinogaline obtained in this way is a crystalline powder with a melting point of 244-245 (with decomposition): The new compound is said to be used as a medicinal product and as an intermediate product.