Serinol → 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide

Participants

Reaction Conditions

Reaction Steps

5-Amino-1,3-benzenedicarboxylic acid di-n-butyl ester (1148 g, 3.91 mol) is loaded into a 10 L reaction vessel containing methanol (7.5 L) and a 1.5M solution of sodium methylate in methanol (0.39 L, 0.59 mol) and 2-amino-1,3-dihydroxypropane (820 g, 9.0 mol) are added thereto. The reaction mixture is then heated to the reflux temperature and kept at this temperature for 4 hours. The mixture is then concentrated to 4 L, cooled to 25° C. and after one night at room temperature it is filtered. The solid on filter is washed with methanol (2×1.3 L) and dried yielding the compound of the title (1215 g, 3.71 mol, yield: 95%).

Provenance & Evidence