CH239683A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents

Description

  

  Process for the preparation of a new benzenesulfonamide derivative. The present patent is a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that a 2-benzenesulfonamido - 5 - diethylmethyl - thiodiazole - (1,3,4), which is in the p-position by reduction has substituents which can be converted into the amino group, treated with a reducing agent.



  The 2- (p-amino-benzenesulfonamido) -5-diethylmethyl-thiodiazole- (1,3,4) obtained in this way melts at 230. The new compound is to be used as a drug and as an intermediate product.



  The 2-benzenesulfonamido-5-diethyl-methyl-thiodiazole- (1,3,4), which contains a substituent which can be converted into the amino group by reduction in the p-position to the sulfonamide group, can be obtained in various ways.

   The implementation of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides with 5-diethylmethyl-thiodiazole- (1,3,4) compounds, which contain a group in the 2-position which forms a 2nd with the benzenesulfonic acid derivative, is particularly suitable -Benzolsulfonamido-5-diethyl methyl thiodiazole (1,3,4) is able to form, especially with 2-amino-5-diethylmethyl thiodiazole (1,3,4)

  . However, the corresponding sulfonamides of the formula RSO, NHY, in which Y denotes a residue which is split off in the subsequent reaction, can also be reacted with 2-halo-5-diethylmethyl-thio-diazolen- (1,3,4) or use other manufacturing methods familiar to those skilled in the art.



  <I> Example </I> In a suspension of <B> 17.1 </B> g of 2-amino-5-diethylmethyl-thiodiazole- (1,3,4) in 45 cm 'of dry pyridine are 22.2 g p-nitrobenzenesulfochloride entered. After the mixture has been heated for hours on the steam bath, the nitro compound is precipitated with water and purified by recrystallization from alcohol. The reduction to the amino compound takes place with tin chloride in concentrated hydrochloric acid.

   After recrystallization from ethyl alcohol, the? \ - (p -amino-benzenesulfonamido) -5-diethyl-methyl-thiodiazole- (1,3,4) melts at 230.



  The p-aminobenzenesulfonamide derivative formed can also be used in the form of its salts, e.g. B. of sodium or calcium isolate.



       Example <I> 2: </I> 17.1 g \? - Amino - 5 - diethylmethyl - tliio- diazol- (1,3,4) are condensed in 25 a 'pyridine with 22 g of p-nitrobenzenesulfochloride. The reaction is terminated by heating for one hour on the water bath.

   The condensation product is precipitated by pouring into ice water and suction filtered. It is then introduced into a boiling mixture of 20 g of iron filings, 300 cm ': 50% alcohol and 1 cm' of concentrated hydrochloric acid, with stirring, and boiled for several hours. The alcohol is distilled off and the reaction mixture is made alkaline with sodium hydroxide solution and filtered hot. From the filtrate, the - (p -amino-benzenesulfonamido) -5-diethylniethyl-thiodiazole (1,3,4) is precipitated in crystalline form with acetic acid .

    Recrystallized from aqueous alcohol it is a white powder of 230 ".



  The reduction can also be carried out with ferro hydroxide in the presence of sodium or calcium hydroxide and water, the sodium or Forms calcium compound of benzene sulfonamide.

 

Claims (1)

PATENT CLAIM: Process for the preparation of a new Benzolsulfonaniidderivates, characterized in that a 2-benzenesulfonamido-5-dietliylmethyl-thiodiazole- (1,3,4), which has a substituent in the p-position which can be converted into the amino group by reduction, with a reducing agent treats. The 2- (p-amino-benzenesulfonamido) -5-diethylniethyl-thiodiazole- (1,3,4) obtained in this way melts at 230. The new compound is to be used as a drug and as an intermediate product.