Hydrochloric Acid → 1-propyl-1H-imidazol-2-amine

Participants

Reaction Steps

A mixture of N-[(1E)-phenylmethylidene]-1-propyl-1H-imidazol-2-amine (0.92 g, 4.31 mmol) and 6N HCl (25 mL) was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated to a residue then taken up in 2M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40M) with CH2Cl2/MeOH/NH4OH (gradient, 950:47:3 to 900:90:10) to give 0.30 g (56%) of brown oil: 1H NMR (400 MHz, CDCl3) δ 6.63, 6.52, 4.00, 3.65, 1.75, 0.95; MS (ESI+) 126.7.

Provenance & Evidence