PROCESSES OF PREPARING ASYMMETRIC DINITROBENZAMIDE MUSTARD COMPOUNDS, INTERMEDIATE COMPOUNDS USEFUL THEREIN AND PRODUCTS OBTAINED THEREFROM

摘要

The invention relates to methods of preparing compounds of formula (II) wherein Z represents -OR<SUP>1 </SUP>or -N(R<SUP>2</SUP>)R<SUP>2a</SUP>-, where R<SUP>1</SUP> is lower alkylene (C<SUB>1</SUB>-C<SUB>6</SUB>), R<SUP>2</SUP> is lower alkyl or H and R<SUP>2a</SUP> is lower alkylene (C<SUB>1</SUB>-C<SUB>6</SUB>) or H;Q is absent when R<SUP>2a</SUP> is H and is otherwise selected from the group consisting of H, -OH and protected forms of -OH; one of X and Y is halogen and the other is -OSO<SUB>2</SUB>R<SUP>3</SUP>, where R<SUP>3</SUP> is selected from the group consisting of lower alkyl (C<SUB>1</SUB>-C<SUB>6</SUB>), phenyl and CH<SUB>2</SUB>phenyl. The method comprises the steps of: (a) reacting a compound of formula (I) with aziridineethanol or a 2-[(2-haloethyl)amino]ethanol in the presence of a metal halide, to form a compound of the formula (III) wherein one of X and E is halogen and the other is hydroxy, and (b) reacting the compound of formula (III) with an alkyl- or arylsulfonyl halide or alkyl- or arylsulfonyl anhydride to obtain a compound of the formula (II). The invention also relates to methods of preparing compounds of formula (IV) from the compounds of formula (II) so obtained, and to novel compounds of formula (IIb) useful as intermediates in these methods.