1-Chloro-2,4-Dinitrobenzene → N2-(2,4-Dinitrophenyl)-N1,N1-diethyl-1,2-ethanediamine

Participants

Reaction Conditions

Reaction Steps

Chloro-2,4-dinitrobenzene 1 (1.00 g, 4.937 mmol) was dissolved in anhydrous EtOH (20 mL) in a small argon purged flask and warmed in an oil bath to 40° C. Addition of N,N-diethylethylenediamine 2a (0.63 g, 5.430 mmol) occurred dropwise. The reaction was stirred at reflux for 24 hours then cooled to room temperature. The mixture was basified by the addition of aqueous 1M ammonium hydroxide solution to adjust pH to 10-11. The solid that precipitated was collected on a sintered glass funnel and briefly dried. Recrystallization of the crude solid from EtOH yielded a yellow powder 3a N′-(2,4-Dinitro-phenyl)-N,N-diethyl-ethane-1,2-diamine. Yield: 0.94 grams (67.4%). 1H NMR (DMSO) δ: 0.99 (t, 6H, J=7.1), 2.56 (m, 4H), 2.70 (t, 2H, J=6.1), 3.49 (q, 2H, J=5.5), 7.19 (d, 1H, J=9.7), 8.28 (dd, 1H, J=9.5, 2.6), 8.67 (d, 1H), 9.05 (br s, 1H); MS (APCI): 283 (MH+, 100%)

Provenance & Evidence