N-(ALPHA-CHLOROALKYL)PHTHALIMIDES

The reaction of formaldehyde with amides and imides to give (N-(hydroxymethyl) amides and -imides 1, followed by conversion of 1 into the N-halomethyl derivatives 2, constitutes an important entry into numerous classes of organic compounds.1 Unfortunately, higher aldehydes generally result in no reaction or in formation of the less synthetically useful N, N’-alkylenebis(amides) 3. Phthalimide, for example, reacts readily with formaldehyde but fails to react with benzaldehyde. N-(α-Chloroethyl)phthalimide has been obtained by the alternative procedure of addition of dry HCl to N-vinylphthalimide, 2 but compounds such as N-(α-chlorobenzyl)-phthalimide obviously are not available from this method. RCONHR' + CH2O → RCONR'CH2OH. © 1979, American Chemical Society. All rights reserved.