GB711322A - Process for the production of hetero-cyclic compounds - Google Patents

Abstract

D 2-Oxazoline compounds of the general formul <FORM:0711322/IV (b)/1> and <FORM:0711322/IV (b)/2> wherein R represents hydrogen, halogen or a nitro, lower (1-4 C) alkoxy or phenyl radical) are manufactured by reacting dichloroacetonitrile with an aminodiol compound of the formula <FORM:0711322/IV (b)/3> under such conditions that the D 2-oxazoline compounds produced undergo practically no hydrolysis. The reaction is preferably carried out under anhydrous conditions (i.e. without a p solvent or in an anhydrous organic solvent), but aqueous solvents may be employed if the reaction time and temperature are suitably controlled (e.g. 3 days at 25-30 DEG C., 24 hours at 50 DEG C. or 6 hours at 70 DEG C.). The preferred reaction temperature in all cases is in the range of 20-75 DEG C., and it is advantageous to use excess of dichloroacetonitrile. When the erythro form of the starting material is used, the oxazoline of the second formula above greatly predominates in the product, whereas the threo form of the starting material yields approximately equal amounts of the two oxazolines, which may be separated by fractional crystallization from an organic solvent. Examples describe the use as starting materials of: (1) D - (-) - threo - 1 - p - nitrophenyl - or DL - threo - 1 - p - bromo - or - methoxy - phenyl - 2 - aminopropane - 1 : 3 - diol; (2) DL - threo- 1 - p - nitrophenyl - 2 - aminopropane - 1 : 3 - diol; (3) DL - erythro - 1 - p - nitrophenyl - 2 - aminopropane - 1 : 3 - diol; (4) D - (-) - threo - 1 - p - nitrophenyl - 2 - aminopropane - 1 : 3 - diol; (5) DL - threo - 1 - (41 - biphenylyl) - 2 - aminopropane-1 : 3-diol. Reference has been directed by the Comptroller to Specifications 698,542 and 704,946.