1,2-Dimethoxyethane → HCID 11950940, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the chloride 21 (2.0 g, 9.03 mmol) and N′-(2-methoxyethyl)-N1-methyl-1,2-ethanediamine (268) (2.38 g, 18.1 mmol) in DME (140 mL) was heated at reflux temperature for 22 h. The solution was cooled to 20° C., the solvent evaporated and the residue purified by column chromatography, eluting with a gradient (2-16%) of MeOH/DCM, to give 1-oxide 30 (1.89 g, 66%) as a yellow solid: mp 107-110° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.89 (br s, 1H, NH), 3.48-3.56 (m, 4H, CH2O, CH2N), 3.36 (s, 3H, OCH3), 3.00 (q, J=7.6 Hz, 4H, H-6, H-8), 2.63-2.71 (m, 4H, 2×CH2N), 2.33 (s, 3H, NCH3), 2.14 (p, J=7.4 Hz, 2H, H-7); 13C NMR δ 158.8, 154.4, 148.8, 143.1, 129.8, 120.5, 114.7, 71.0, 58.8, 56.7, 56.0, 42.4, 38.8, 33.1, 32.3, 25.7; HRMS (FAB+) calcd for C16H24N5O2 (MH+) m/z 318.1930, found 318.1930.

Provenance & Evidence