GB705078A - Cyclic sulphites and carbonates of 1-p-nitrophenyl-2-haloacetamidopropane-1,3-diols and processes for the production of the same - Google Patents

Abstract

Cyclic sulphites of the general formula <FORM:0705078/IV(b)/1> (wherein R represents a halogenated acetyl radical) are manufactured by reacting a dl- or l-q -1-p-nitrophenyl-2-haloacetamidopropane -1:3- diol with a thionyl halide in an excess of the thionyl halide as solvent at a temperature below about 50 DEG C. (preferably 20-35 DEG C.) under anhydrous conditions, adding an inert organic solvent (e.g., chloroform, methylene dichloride, ethylene dichloride, benzene, xylene, carbon tetrachloride, ether or toluene) and collecting the cyclic sulphite thereby precipitated from the reaction mixture. Examples describe the action of thionyl chloride on l- and dl-q -1-p-nitrophenyl-2-dichloro-, -dibromo-and-difluoroacetamidopropane -1:3- diol, dl-q -1-pnitrophenyl -2-chloro- and -iodo-acetamidopropane -1:3-diol, and l-q -1-p-nitrophenyl-2-fluoro- and-fluorochloro-acetamidopropane -1:3-diol, and of thionyl bromide on l-q -1-p-nitrophenyl-2-chloroacetamidopropane -1:3-diol and dl-q -1-p-nitrophenyl-2- fluoroacetami dopropane -1:3-diol. Cyclic carbonates of the general formula <FORM:0705078/IV(b)/2> are manufactured by reacting a dl- or l-q -1-p-nitrophenyl-2-haloacetamidopropane -1:3- diol with phosgene at a temperature below about 20 DEG C. (preferably -10 DEG to +10 DEG C.) in an inert organic solvent under anhydrous conditions or in a substantially anhydrous tertiary amine. Examples describe the treatment of chloramphenicol in ethylene dichloride and of dl-q -1 - p - nitrophenyl - 2 - dichloracetamidopropane -1:3- diol in pyridine. Other tertiary amines specified are N-ethylpiperidine, dimethylaniline, N-methylmorpholine and tri-ethylamine.ALSO:Compounds possessing antibiotic properties, of the general formula <FORM:0705078/VI/1> (wherein R represents a halogenated acetyl radical and Y an -SO- or -CO- group), are suitable for incorporation into uncoated pills, elixirs, syrups and candies for oral administration.