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N -acylation and  O -acylation of pseudoephedrine are studied by using aroyl chlorides and/or ethyl chloroformate as acylating agents. Thus, treatment of pseudoephedrine or its salt with benzoyl or  p -nitrobenzoyl chlorides affords the corresponding  N - or  O -acylated products  2a, b ,  3a, b  and  4 . Also, pseudoephedrine  1  was allowed to react with ethoxymethylenemalononitrile to yield 2-hydroxy-1-methyl-2-phenylethyl](methyl)amino}methylene)malononitrile  (5) . New oxazolidine derivatives  6a–c  were conveniently synthesized in high yields from the reaction of  1  with different bis(methylthio)yledinenitriles. X-ray crystallographic study of  4  revealed that the compound crystallized in orthorhombic system. The structure is stabilized by the intermolecular interactions as well as a network of hydrogen bond contacts, conformed parallel layers.

Synthesis and X-ray crystallography of new N-, O- acyl pseudoephedrines