Focus: 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMTMM)

Abstract

The use of alkoxychloro-1,3,5-triazines as an alternative to carbodiimides in generating activated esters of carboxylic acids for the preparation of amides, esters and anhydrides has been known since 1985.^[1] The most commonly employed reagent in this class is DMTMM (1), [3945-69-5], a colourless, air- and water-stable solid (m.p. 116–117˚C) which is commercially available (Acros Organics), or easily prepared by the reaction of N-methylmorpholine with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT [3140-73-6]) in tetrahydrofuran.^[2] Compound (1) has frequently been prepared in situ, but it can be stored for several months in the refrigerator without decomposition and is reported to not possess the irritant properties of CDMT.