Patent GB-581934-A (GB)
Title: Manufacture of para-aminobenzene sulphonacylamides
IPC: C07C311/45
Filed: 1944-03-10
Abstract: Para - aminobenzenesulphonacylamides are prepared by reacting a sulphonamide of the benzene series containing in the para position a group containing nitrogen which is convertible into an amino group by hydrolysis or reduction or a salt of such a sulphonamide with a carboxylic acid or a functional derivative thereof containing a condensed ring nucleus, which may contain substituents incapable of forming salts.  The condensation is preferably conducted in the presence of acid binding agents such as pyridine, and also if desired in the presence of a catalyst for splitting off hydrogen halide.  The preferred functional derivatives referred to above are the acid chloride and the acid amide.  The sulphonamides which may be used in the present invention are the same as those named in the parent Specification. In an alternative form of the invention a sulphonic acid halide of p  the benzene series containing in the para position an amino group or a group containing nitrogen which is convertible into an amino group by hydrolysis or reduction is treated with an amide of a carboxylic acid containing a condensed ring nucleus which may contain substituents incapable of forming salts.  Carboxylic acids mentioned include a number of substituted 1-naphthoic acids, and 2-naphthoic acids also indene-, anthracene-, and phenanthrene - carboxylic acids.  In examples: (1) a pyridine solution of p-nitrobenzene sulphonamide is treated with 2-naphthoic acid chloride, and the product reduced with iron and hydrochloric acid to give 4-aminobenzene-sulphon naphthoyl-(21)-amide.  (2) a pyridine solution of p-nitrobenzene sulphonamide is treated with 3-methoxy-2-naphthoic acid chloride and the product reduced as in example (1).  (3) A pyridine solution of p-nitrobenzene sulphonamide is treated with 1-methoxy-2-naphthoic acid chloride and the product reduced as in example (1).  (4) A pyridine solution of p-nitrobenzene sulphonamide is treated with 4-methyl-1-naphthoic acid chloride and the product reduced as in example (1).  Other compounds named as being obtained in exactly the same manner are 4 - aminobenzene - sulphon - 21 - methyl - 11 - naphthoyl amide.  4 - Aminobenzene - sulphon - 11 - methyl - 21 - naphthoyl amide.  4 - amino - benzene - sulphon - 31 - methyl - 21 - naphthoyl - amide.  4 - Aminobenzene - sulphon - 31 : 41 - dimethyl - 11 - naphthoylamide.  4 - Aminobenzene - sulphon - 21 - ethyl - 11 - naphthoylamide.  4 - aminobenzene - sulphon - 41 - ethyl - 11-naphthoylamide.  (5) A pyridine solution of p-nitrobenzene sulphonamide is reacted with 1-naphthoyl chloride and the product reduced as in example (1).  The same product is obtained if 1-naphthoic acid amide is used instead of the acid chloride.  (6) a pyridine solution of p-nitrobenzene sulphonamide is reacted with 1-methyl-indene-2-carboxylic acid chloride and the product reduced as in example (1).  Other compounds named as being obtained in exactly the same manner are 4-aminobenzene-sulphon - hydridene - 51 - carboxylic acid amide.  4 - aminobenzene - sulphon - phenanthrene - 91 - carboxylic acid amide. 4-aminobenzene-sulphon - anthracene - 91 - carboxylic acid amide.  Specifications 541,958 and 581,932 are referred to.