4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: An efficient condensing agent leading to the formation of amides and esters

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) was quantitatively synthesized by the coupling of 2-chloro-4,6-dimethoxy-1, 3,5-triazine (CDMT) and N-methylmorpholine (NMM) in THF, and characterized. Condensation of carboxylic acids and amines by DMTMM proceeded effectively in THF to give the corresponding amides in good yields. The corresponding esters can be obtained by esterification of carboxylic acids with DMTMM in methanol, ethanol, isopropyl alcohol, or t-butyl alcohol in the presence of NMM. The amount of alcohols can be reduced to a stoichiometric amount by c onducting the reaction in THF. Since the reactions proceed under atmospheri c conditions without drying of the solvent, and the co-product (4,6-dimetho xy-1,3,5-triazin-2(1H)-one) arising from DMTMM after condensation can be re adily removed by extraction, this method is a very practical one. (C) 1999 Elsevier Science Ltd. Ail rights reserved.