Patent GB-508794-A (GB)
Title: Manufacture of chloro-methyl compounds of sulphonamides
IPC: C07C311/02
Filed: 1938-01-04
Abstract: 508,794. Sulphonamide derivatives. GROVES, W. W. (I. G. Farbenindustrie Akt.- Ges.) Jan. 4, 1938, No. 211. [Class 2 (iii)] Chloromethyl compounds of sulphonamides are manufactured by causing a sulphonamide which has at least one exchangeable hydrogen atom at the amide nitrogen and also contains a hydrocarbon radicle having at least 4 carbon atoms, which may contain, substituents and /or may be interrupted by at least one oxygen, sulphur of nitrogen atom, to react with formaldehyde or a polymer thereof and hydrogen. chloride at ordinary or raised temperature, or by causing. hydrogen chloride to react with a methylol compound obtained by the reaction of formaldehyde or a polymer thereof with a sulphonamide as denned above. Suitable sulphonamidea are : butytsulphonamide, isohexylsulphomethylamide; dodecylsulphonamide, octadecylsulphonamide, chloroctadecylsulphonamide (obtained by the simultaneous action of sulphur dioxide and chlorine on n-octadecane, the chlorine being caused to act until in addition to that in the sulphochloride group a further chlorine atom has entered the carbon chain, and treatment of the. chloroctadecylsulphochloride with ammonia), 9 : 10-dichloroctadecyl: sulphomethylamide (obtained by splitting up oleylisothiourea, obtained from oleyl chloride-. and thiourea, with chlorine and treating the resulting 9: 10-dichloroctadecylsulphochloride with methylamine), p - butylphenoxyethanesulpho-N-n-hexylamide (obtained by treating the chloride of p-butylphenoxyethanesulphonic acid, obtained by condensing sodium p-butylphenolate. with the sodium salt of chlorethanesulphonic acid, with n-hexylamine), p-toluenesulphonamide and p - butylbenzenesulphonamide. The reaction may be carried out by dissolving or suspending the sulphonamide in aqueous formaldehyde and saturating with hydrogen chloride, or by dissolving the sulphonamide in, an. organic solvent, e.g. benzene, toluene, xylene, methylene chloride, carbon tetrachloride, chlorobenzene or ether, adding solid formaldehyde and introducing hydrogen chloride. The products may be used for the treatment of materials such as textiles, leather, paper or plasticmasses. In examples : (1) octadecylsulphonamide (obtainable by the action of liquid ammonia, on octadecylsulphochloride) is dissolved in methylene chloride, paraformaldehyde is added and hydrogen chloride introduced into the cold solution ; (2) a larger proportion of paraformaldehyde is employed in the process of (1): y (3) isohexylsulphomethylamide (obtamed by condenising isohexyl chloride with thiourea, converting the product into the sulphochloride and reacting this with liquid monomethylamine) is reacted with paraformaldehyde and hydrogen chloride in carbon octadecylsulphomethylolamide is treated with hydrogen chloride in : methylene chloride; (5) a hydrocarbon fraction obtained in the hydrogenation of carbon monoxide and containing about 14 carbon atoms is treated with sulphur dioxide and chlorine with exposure to ultra-violet light,- the sulphochloride, obtained is treated with liquid ammonia and the resulting sulphonamide in material may be replaced by hard paraffin ; (6) tetradecylsulphonamide, obtained as in (5), is mixed with aqueous formaldehyde and hydrogen chloride is introduced; (7) n-propyl-N-octadecylsulphonamide (obtained by reacting n, propylsulphochloride with octadecylamine) is reacted with paraformaldehyde and hydrogen chloride in benzene; (8) p-toluenesulphomethylolamide is treated with hydrogen chloride in chlorobenzene; (9) 1-stearylemino-2-nitro- _ benzene-4-sulphonamide (obtained by, acylating 1 - amino - 2-nitrobenzene-4-sulphonamide with stearic acid chloride) is reacted with paraformaldehyde and hydrogen chloride in methylene chloride; (10) 1-methoxy-2-nitrobenzene-4-sulphonamide is similarly reacted (11) p-isododecylcyclohexanol is condensed with sodium chlorethanesulphonate, the product is treated with phosphorus pentachloride and then with liquid ammonia, and the resulting sulphonamide is reacted with paraformaldehyde and hydrogen chloride in ether.