CH207672A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents

Description

  

  Process for preparing an aminobenzenesulfonic acid amide compound. According to the invention described in Patent No. 199315, certain aminoacyl and oxyacylaminobenzenesulfonic acid amides and their substitution products are distinguished by their action against bacterial infectious diseases.



  The subject of the present patent is a process for the preparation of an aminobenzenesulfonic acid amide compound, which is characterized in that 4- (4 'nitrobenzoisulfonamido) - benzenesulfonmonomethylamide is reduced to 4- (4'-aminobenzenesulfonamido) 7benzenesulfonomethylamide by the action of a reducing agent adorns. Iron filings in counter-throw are preferably used as reducing agent; of very dilute acetic acid.

   But you can also use other common reducing agents such. B. reduce the starting compound in aqueous-alkaline solution with sodium hydrosulfite. The reaction product can be separated off in the usual way from the reduction mixture. You can, for example, make the reaction mixture alkaline, suck off the iron sludge and remove the reaction product from the filtrate by acidification with acids, e.g. B. acetic acid, from cases. After recrystallization, e.g. B.

    From dilute alcohol, the 4- (4'-aminobenzenesulfonamido) -benzenesulfonomethylamide which can be obtained forms colorless crystals with a melting point of 141. It is sparingly soluble in cold water, dissolves in alkalis and is said to find therapeutic applications.

    <I> Example: </I> 50 g of 4- (4'-nitrobenzenesulfonamido) -ben- solsulfonmonomethylamide (produced by the condensation of 4-nitrobenzenesulfonomethylamide with 4-aminobenzenesulfonomethylamide in pyridine, from alcohol almost white crystals with a melting point of 190 to 191) to a boiling mixture of 100 g of iron filings, 500 cm 'of water and 5 cm' of acetic acid.

   After the vigorously stirred mixture has been boiled for several hours at back t2, it is cooled, made alkaline with dilute sodium hydroxide solution and sucked off the iron. By acidifying the filtrate with acetic acid, the 4 - (= 1'-amino) zolsLZl-fonamido) -benzenesulfononomethylamide is precipitated. After unicrystallization from alcohol, it forms colorless crystals at the melting point 141.

   Instead of reducing with iron, the nitro compound named as the starting material can also be reduced with other common reducing agents. For example, you can dissolve the nitro compound in aqueous sodium hydroxide solution and add solid sodium hydrosulphite with gentle heating until the solution is permanently decolorized.

   The amino compound is precipitated out by acidifying the solution with acetic acid.

 

Claims (1)

PATENT CLAIM: A process for the production of an amino lienzolsitlfonsäitreaniidverliindnng, characterized in that 4- (4'-nitrobenzenesulfonamido) - benzenesulfonmonomethylamide is reduced by the action of a reducing agent to 4- (4'-aminobenzenesulfonamido) -benzenesulfonamethylamido. The 4- (<1'-aniinobenzenesulfonamido) -benzenesulfonmonomethylamide thus obtainable forms colorless crystals with a melting point of 141. UN TER CLAIM 1. Process according to claim, characterized in that iron filings and dilute acetic acid are used as reducing agents. ?. Process according to patent claim, characterized in that the reduction is effected in an aqueous alkaline solution by means of sodium hydrosulfite.