Patent GB-589352-A (GB)
Title: Manufacture of ú­-aminobenzene-sulphone trimethylacrylic acid amide
IPC: C07C311/37
Filed: 1944-11-11
Abstract: Acylated p-aminobenzene sulphonamides constituting an improvement in or modification of the invention of the parent Specification and stated to be particularly effective against staphylococci, are obtained by reacting sulphonamides of the benzene series carrying a nitrogen-containing group in the p-position, or their metal salts, with trimethyl acrylic acid or its functional derivatives, if necessary or desirable in presence of catalysts or acid-binding agents and, if desired or necessary, converting the p-positioned group containing nitrogen into an amino group, e.g. by reduction. Alternatively, similar products are obtained by treating benzenesulphohalides carrying a nitrogen-containing group in the p-position with salts of trimethylacrylic acid amide and similarly converting the p-positioned group containing nitrogen into an amino group, if desired or necessary.  Suitable sulphonamides are p-aminobenzene-, alkyl or aralkyl-aminobenzene-, p - acylaminobenzene- or p - nitrobenzene sulphonamides, or the corresponding nitroso, azo, azoxy, hydrazo or azomethine compounds, and sodium p-nitrobenzene sulphonamide or potassium p-acetylaminobenzene sulphonamide.  In examples: (1) p-acetylaminobenzene sulphonamide and trimethylacrylic anhydride are heated together adding hydrochloric acid, and heating with dilute caustic soda to yield p-aminobenzene sulphone trimethylacrylic acid amide; (2) p-acetylaminobenzene sulphonamide, trimethylacrylic acid and phosphorus pentoxide are heated in chlorobenzene, water is added, the mixture is steam-distilled and the residue is treated as in (1); (3) p-nitrobenzenesulphonamide, trimethylacrylic acid and phosphorus pentoxide are reacted as in (2) to isolate p-nitrobenzene sulphone-trimethylacrylic acid amide; (4) sodium p-nitrobenzene sulphonamide, suspended in nitrobenzene, is mixed with trimethylacrylic acid chloride, diluting, making alkaline, extracting the filtrate with ether and acidifying to precipitate p-nitrobenzene sulphone-trimethyl acrylic acid amide, which is reduced by B<\>aechamp's method to the corresponding p-aminobenzene sulphone; (5) p-acetylaminobenzene sulphonamide, chlorobenzene and trimethyl acrylic acid chloride are heated with a catalyst such as copper powder, aluminium chloride, ferric chloride, stannic chloride or cupric chloride to form p-aminobenzene sulphone-trimethyl acrylic acid amide; (6) p-acetylaminobenzene sulphonamide, calcined sodium carbonate and trimethylacrylic acid chloride are heated to yield the product of (5); (7) 4-carbethoxyaminobenzene sulphonamide, or the corresponding carbomethoxy compound, is heated with trimethylacrylic acid chloride and copper powder in chlorobenzene to obtain the appropriate 4-carbalkoxyaminobenzene sulphone-trimethylacrylic acid amide, which is hydrolysed by heating for 15 minutes in 2N caustic soda in the water-bath; (8) trimethylacrylic acid amide and sodamide heated in toluene, then treated with p-nitrobenzene sulphochloride in toluene and the mass is heated to form 4-nitrobenzene-N1-(trimethylacrylic)-sulphonamide, from which the corresponding amino compound is obtained by reduction. Trimethylacrylic acid anhydride is obtained from dry trimethyl sodium acrylate and trimethylacrylic acid chloride.  Specification 541,958 is referred to.