Patent GB-760051-A (GB)
Title: Sulphonamides containing urethane groups
IPC: C07D295/26
Filed: 1955-10-06
Abstract: The invention comprises sulphonamides containing urethane groups and having the formula <FORM:0760051/IV(b)/1> in which R is a divalent aromatic hydrocarbon radical and R1O is the residue of a saturated or unsaturated substituted or unsubstituted aliphatic, cycloaliphatic aromatic or heterocyclic alcohol and R2 and R3 are hydrogen atoms or monovalent hydrocarbon radicals or monovalent substituted hydrocarbon radicals, or heterocyclic nuclei, or R2 and R3 together with the adjacent nitrogen atom represent a heterocyclic nucleus. Sulphonamides containing urethane groups are prepared by a process which comprises reacting at a temperature below 40 DEG  C, an isocyanate-aromatic sulphonic acid chloride with an alcohol as hereinbefore defined thereby to obtain the corresponding urethane sulphonic acid chloride, and reacting the urethane sulphonic acid chloride thus obtained with ammonia or a primary or secondary amine. Suitable alcohol starting materials are aliphatic, cycloaliphatic, aromatic and heterocyclic alcohols, which may be saturated or unsaturated and they may be substituted with substituents which do not contain hydrogen that can be detected by the Zerewitinoff method. Alcohols specifically mentioned include methanol, butanols, allyl alcohol, propargyl alcohol, ethylene glycol, glycerol, ether alcohols such as glycol monomethyl ether, ester alcohols such as glycol monoformate, lactic acid ethyl ester, glycol chlorhydrin, aminoalcohols such as dimethylaminoethanol, benzyl alcohol, phenyl ethyl alcohol, benzohydrol, cyclohexanol, tetrahydro- and decahydro-naphthols.  Amino compounds mentioned include aliphatic, cycloaliphatic, aromatic or heterocyclic amines and the radicals attached to the nitrogen atom may be saturated or unsaturated and substituted by halogen, hydroxy, nitrile, ether, ester or tertiary groups or by groups causing solubility in water such as sulphonic acid or carboxyl groups.  A solution of the isocyano-sulphonic acid chloride in an inert solvent may be added to the alcohol, optionally in an inert solvent, e.g. benzene, tetrahydrofuran or dioxane.  The solution of urethane thus obtained is then added to a solution of the amino compound in an inert solvent, in the alcohol used for the first step or in another alcohol.  When amines containing sulphonic acid or carboxyl groups are employed the solution of the urethane in a water-miscible solvent may be added to an aqueous solution of the former.  In examples N-(4-sulphonamidophenyl) - O - n - butyl urethane is obtained by reacting n-butyl alcohol with p-chlorosulphonyl phenylisocyanate in benzene and adding the product to a solution of ammonia in butanol (1); N - (4 - sulphonamidophenyl) - O - isopropyl urethane is obtained similarly using p-chlorosulphonyl phenyl isocyanate, isopropanol and ammonia (2); N-4-carbomethoxy-sulphanilamide is similarly obtained using methanol in a similar process (3); N-4-carboethoxy-sulphonilamide is similarly obtained using ethanol (4); N - 4 - (carbo - n - propyloxy) - sulphanilamide is similarly obtained (5); N-(sulphonamidophenyl) - O - benzylurethane is similarly obtained using benzyl alcohol (6); p-carbobutoxyamino - benzene - sulphonic acid - butylamide is similarly obtained using n-butanol (6); p-carbobutoxy - amino - benzene - sulphonic acid-dibutylamide is similarly obtained using n-butanol and di-n-butylamine (7); p-carbobutoxy aminobenzene sulphonic acid mono-n butyl amide is similarly obtained using n-butylamine (8); 1 carbobutoxy - aminonaphthalene - 6 - sulphonic acid - amide is similarly obtained using 6-chlorsulphonyl-naphthyl - 1 - isocyanate, n - butanol and ammonia (9); the compound represented by the formula <FORM:0760051/IV(b)/2> is obtained by reacting p-chlorosulphonyl-phenylisocyanate in benzene with methanol and adding the product to a hot aqueous solution of p-sulphanilic acid neutralized with sodium carbonate and maintaining the mixture neutral or slightly alkaline with sodium hydroxide (10); N - (4 - sulphonamidophenyl) - O - b  - chloroethyl-urethane is obtained by reacting p-chlorosulphonyl-phenylisocyanate with b -chloroethyl alcohol in benzene and adding the product to a solution of ammonia in methanol (11); the product of the formula <FORM:0760051/IV(b)/3> is similarly obtained using N-(b -hydroxyethyl)-N-ethyl-aniline in the first step (12); in a similar process N - (b  - hydroxyethyl) - N - n - butylaniline is employed in the first step (13); in a similar process N - (b  - hydroxyethyl) - N - n-butyl-m-toluidine is employed (14); in a similar process to (13) di-n-butylamine in benzene is employed instead of ammonia in the second step (15); in a similar process to (1) N-(3-sulphonamido - phenyl) - O - n - butyl - urethane is obtained using m-chloro-sulphonyl-phenylisocyanate (16); in a process similar to (1) the product of the formula <FORM:0760051/IV(b)/4> is obtained using m-chlorosulphonyl phenylisocyanate, butanol and b -aminoethanol (17); 3:4-dichlorobenzyl alcohol is reacted with p-chlorosulphonyl phenylisocyanate in benzene and the product is reacted with ammonia in methanol (18); or 3 : 4-dichlor-aniline in methanol (19); methanol is similarly reacted with p-chloro-sulphonyl phenyl isocyanate and the product is reacted with piperidine (20); and 2-amino-pyridine (21).  Specification 748,166 is referred to.