Patent GB-786059-A (GB)
Title: N-substituted sultams and a process of production
IPC: C07D275/02
Filed: 1954-04-15
Abstract: The invention comprises N-substituted sultams of the general formula <FORM:0786059/IV (a)/1> wherein R represents an aliphatic straight or branched chain saturated hydrocarbon bridge containing 3 or 4 carbon atoms, and R1-X-represents CH3 or X represents -CH2-, -SO2- or -CO- and R1 represents a hydrocarbon or a substituted hydrocarbon radical, and the preparation thereof by reacting a sultam of the general formula <FORM:0786059/IV (a)/2> wherein R has the above significance, or an N-alkali metal salt thereof, with the required hydrocarbon or substituted hydrocarbon halide, carboxylic halide or sulphonic acid halide.  The process may be carried out in the presence of sodium or potassium hydroxide solution.  The reaction with the alkali metal sultams may be carried out with or without the use of a diluent. When a diluent is used it is preferably to suspend or dissolve the alkali metal sultam in water or in an organic solvent such as benzene, ether or dioxan.  The reaction of the sultam reactant itself may be effected in the presence of an alkali metal hydroxide or an alkali metal carbonate with the sultam reactant dissolved in water or an organic solvent.  The group R1-X-, in addition to representing a methyl group, may also represent an ethyl, benzyl, acetyl, benzoyl p-nitrobenzoyl, p-toluene-sulphonyl or 4-aminobenzene-sulphonyl radical, or a 4-aminobenzenesulphonyl radical substituted on the nitrogen atom by an acyl radical, e.g. the acetyl radical.  Suitable sultam reactants referred to are gamma-propane sultam, alpha-methyl-gamma-propane sultam, beta-methyl-gamma-propane sultam and delta-butane sultam.  In the examples, the following compounds are prepared by the process referred to above: N - (benzoyl)-, N - (p - toluene - sulphonyl)-, N - (4 - acetamino - benzene - sulphonyl - 1)-, N - methyl-, N - benzyl-, and N-acetyl - alpha - methyl - gamma - propane sultam, N - (p - nitro - benzoyl)- and N - (p-toluene - sulphonyl) - delta - butane sultam, and N - acetyl - gamma - propane sultam.  N - (4-amino - benzene - sulphonyl - 1) - alpha - methyl-gamma-propane sultam is also prepared by treating the corresponding N-(4-acetamino-benzene-sulphonyl-1) compound with hydrochloric acid.  The above process for the preparation of the N-substituted sultams may be modified in that the sultams of the general formula <FORM:0786059/IV (a)/3> wherein R has the above significance, are prepared by reacting the required aliphatic amines with hydrogen chloride, the hydrochlorides formed are treated with a mixture of sulphur dioxide and chlorine, preferably while being irradiated with octinic light, to form aminoaliphatic sulphochloride hydrochlorides which are then treated with a caustic base.  The alkali metal salts of the sultams are then formed by treatment with an alkali metal in an inert solvent such as benzene or ether, by treatment with an alkali metal alkoxide in alcoholic solution, or by treatment with alkali metal hydroxide.  In preparations: (1) delta-butane sultam and alpha-methyl-gamma-propane sultam are prepared by forming n-butylamine hydrochloride which is then sulpho-chlorinated to form aminobutane-sulpho-chloride and on treatment with caustic soda solution forms a mixture of the required sultams which are then separated; (2) the potassium salt of delta-butane sultam is prepared using methanolic potassium hydroxide; (3) the sodium salt of alpha-methyl-gamma-propane sultam is prepared using sodium in benzene and methanolic sodium methoxide; (4) gamma-propane sultam is prepared as in (1) from n-propylamine; and (5) the sodium salt of gamma-propane sultam is prepared using sodium dissolved in methanol.  Starting materials.  1 - Methylamino - butane sulphonic acid-(3) and 1-benzylamino-butane sulphonic acid-(3) are prepared by treating N-methyl - alpha - methyl - gamma - propane sultam and N - benzyl - alpha - methyl - gamma - propane sultam respectively with hydrochloric acid.