GB621644A - Manufacture of derivatives of oxazolidine-2:4-dione - Google Patents

Abstract

Derivatives of oxazolidine 2 : 4 dione of the general formula <FORM:0621644/IV (b)/1> where R1 and R2 are hydrogen at the same or different alkyl aryl or aralkyl radicals and R3 is an alkyl or aralkyl residue containing as substituents one or more of the following, oxygen, nitrogen sulphur or halogen, are prepared by heating the alkali metal salts, such as the sodium salt of an oxazolidine-2 : 4-dione optionally substituted by radicals R1 and R2 in the 5-position with an alkyl or aralkyl halide substituted by an oxygen, nitrogen, sulphur, or another halogen atom. The reaction is preferably carried out in alcoholic solution or in solution in acetone or dioxane. The alkali metal salts of the oxazolidine dione are prepared by reacting the oxazolidine dione with an alkali metal carbonate. When the radical R3 contains a basic nitrogen group salts may be prepared by the action of inorganic or organic acids and where the nitrogen atom is a tertiary nitrogen atom quaternary salts may be obtained by known methods, e.g. the action of alkyl halides, aryl sulphonic esters or iodoaliphatic esters. In examples: (1) the sodium salt of 5 : 5-dimethyloxazolidine-2 : 4-dione is treated with ethylene chlorohydrin to give 3-b -hydroxyethyl - 5 : 5 - dimethyloxazolidine - 2 : 4 - dione; (2) by using a -chlorohydrin in place of ethylene chlorohydrin in (1) 3-b : g -dihydroxypropyl-5 : 5-dimethyloxazolidine-2 : 4-dione is prepared; (3) using g -diethylamino-b -hydroxypropyl chloride in place of ethylene chlorohydrin in (1), 3-b -hydroxy-g -diethylaminopropyl-5 : 5-dimethyloxazolidine-2 : 4-dione is prepared; (4) to (8) there are also prepared according to the invention the acetoacetate of 3-b -hydroxyethyl-5 : 5-dimethyloxazolidine - 2 : 4 - dione; 5 : 5 - dimethyl-3-b -methylthioethyloxazolidine-2 : 4-dione; 3-b -hydroxyethyl-5 : 5-diphenyloxazolidine-2 : 4-dione; 3-b -hydroxyethyl-5-methyl-5-phenyloxazolidine-2 : 4-dione; 3-b -bromoethyl-5-methyl-5-ethyloxazolidine-2 : 4-dione; (9) 3-b -hydroxy-g -diethylaminopropyl-5 : 5-dimethyloxazolidine-2 : 4-dione hydrochloride is prepared by treating the base with hydrogen chloride; (10) the product of (3) is treated with methyl iodide to give the quaternary methyl ammonium iodide and (11) the product of (3) is treated with methyl-p-toluene sulphonate to give the methyl-p-toluene sulphonate of the base. 5 : 5-Dimethyloxazolidine is prepared as its sodium salt by reacting urea and ethyl-a -hydroxyisobutyrate in ethyl alcohol in the presence of sodium ethoxide.