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

HRID 2074442Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([N:16]([CH2:20][CH3:21])[CH2:17][CH2:18][NH2:19])[CH3:15].[OH-].[NH4+]>CCO>[N+:11]([C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH:19][CH2:18][CH2:17][N:16]([CH2:20][CH3:21])[CH2:14][CH3:15])([O-:13])=[O:12]

Participants

Conditions

Temperature: 40 °C

Procedure

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%)

Workup

temperatureat reflux for 24 hours
temperaturethen cooled to room temperature
customThe solid that precipitated
customwas collected on a sintered glass funnel
custombriefly dried
customRecrystallization of the crude solid from EtOH

Sources & evidence

ORD record: ord-7024822511124f5383b5bda343a57f7f
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919510B2

Reaction notes

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