2-Chloroimidazoline sulfate → 2-[4-(5-Methoxythien-2-ylmethyl)phenyl]amino-imidazoline

Participants

Reaction Conditions

Reaction Steps

To a solution of [4-(5-methoxythien-2-ylmethyl)-phenylamine (145 mg, 0.66 mmol) in acetonitrile (10 ml) was added 2-chloro-2-imidazoline sulfate (155 mg, 0.76 mmol) at 20-25° C. under nitrogen. The resulting suspension was heated at 80° C. for 1.5 hours. The mixture was diluted with dichloromethane and washed with 10% sodium hydroxide, water, dried (Na2SO4), and concentrated to dryness. Purification by preparative TLC, eluting with ethyl acetate/methyl alcohol/isopropylamine, gave 2-[4-(5-methoxythien-2-ylmethyl)phenyl]amino-imidazoline (132 mg, 70%) as a yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.12 (d,J=8.4Hz, 2H), 6.93 (d,J=8.4 Hz, 2H), 6.39 (dt, J=3.7, 1.1 Hz, 1H), 5.98 (d,J=3.7 Hz, 1H), 3.92 (bs, 2H), 3.82 (S,3H), 3.52 (S ,4H), 3.15-3.35 (broad, 2H). 2-[4-(5-methoxythien-2-ylmethyl)phenyl]amino-imidazoline oxalate, m.p. 121.8-122.8° C.

Provenance & Evidence