Diethyl Ether → Diisopropylether ethyl acetate

Participants

Reaction Steps

Similar reaction of crude 5-chloro-2,4-dinitrobenzoyl chloride in Et2O with 4-[2-(methylamino)ethyl]morpholine (2 equiv) in water, followed by chromatography of the product on alumina-90, eluting with EtOAc, gave 5-chloro-N-methyl-N-[2-(4-morpholino)ethyl]-2,4-dinitrobenzamide (48%), mp (EtOAc/iPr2O) 123-123.5° C. 1H NMR [(CD3)2SO] [rotamer mixture] δ8.94 & 8.94 (2xs, 1H, H-3), 8.13 & 8.09 (2xs, 1H, H-6), [3.63-3.54 (m), 3.51, t (J=4.6 Hz) & 3.28-3.18(m), 6H, O(CH2)CH2, N(CH3)CH2], 3.05 & 2.89 (2xs, 3H, CH3), [2.57 (t, J=6.6 Hz), 2.50-2.38 (m) & 2.25 (t, J=4 3 Hz), 6H, CH2N(CH2)CH2]. Anal. Calcd. for C14H17ClN4O6: C, 45.11,H, 4.60; N, 15.03. Found: C, 45.01;H, 4,43, N, 15.02%.

Provenance & Evidence