M. Kunishima, Chiho Kawachi, J. Monta
Nov 12, 1999
Citations
7
Influential Citations
331
Citations
Quality indicators
Journal
Tetrahedron
Abstract
Abstract 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 caiboxylic acids with DMTMM in methanol, ethanol, isopropy1 alcohol, or t-butyl alcohol in the presence of NMM. The amount of alcohols can be reduced to a stoichiometric amount by conducting the reaction in THF. Since the reactions proceed under atmospheric conditions without drying of the solvent, and the co-product (4,6-dimethoxy-1, 3,5-triazin-2(1H)-one) arising from DMTMM after condensation can be readily removed by extraction, this method is a very practical one.