Cyanogen Bromide → 4-(3-Bromophenyl)-1,4-dimethylimidazolidin-2-imine

Participants

Reaction Steps

To a solution of 2-(3-bromophenyl)-N1-methylpropan-1,2-diamine (0.12 g, 0.50 mmol) in EtOH (10 mL) was added BrCN (0.073 g, 0.70 mmol, 1.4 eq). The mixture was stirred at RT for 16 h and then concentrated in vacuo. The residue was redissolved in CHCl3 (20 mL) and the solution was washed with 15% NaOH (10 mL). The aqueous layer was extracted with CHCl3 (3×10 mL) and the combined organic layer was dried (MgSO4), and concentrated to give 0.14 g (100%) of 4-(3-bromophenyl)-1,4-dimethylimidazolidin-2-imine (CD4; R1=Me, R4=Me) as a colorless oil. 1H NMR (CDCl3) δ 7.42 (t, J=1.7 Hz, 1H), 7.35 (dd, J=8.1, 1.7 Hz, 2H), 7.15 (t, J=8.1 Hz, 1H), 3.62 (d, J=9.3 Hz, 1H), 3.53 (d, J=9.0 Hz, 1H), 3.08 (s, 3H), 1.56 (bs, 3H). MS (ESI) m/e 268.1, 270.1 (M+H)+.

Provenance & Evidence