Mechlorethamine → HCID 68594997, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-pyridyl acetonitrile hydrochloride (1.0 g, 6.47 mmol) in DMSO (8 mL) was treated with sodium hydride (0.735 g, 29.11 mmol) portionwise. The resulting suspension was stirred at 23° C. for 30 minutes. 2-Chloro-N-(2-chloroethyl)-N-methylethanamine (1.37 g, 7.11 mmol) was then slowly added over 5 minutes, then the suspension was heated at 65° C. overnight. The reaction was then diluted with 1N hydrochloric acid and washed with ethyl acetate (2×). The aqueous phase was basified with 5N sodium hydroxide and extracted with ethyl acetate (3×). The combined extracts were washed with water (5×), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil (0.200 g, 15%) which was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ ppm: 2.10-2.17 (3H, m), 2.31-2.37 (1H, m), 2.42 (3H, s), 2.47-2.57 (2H, m), 3.01 (2G, d, J=12.6 Hz), 7.45 (2H, dd, J=4.55 and 1.52 Hz), 8.68 (2H, dd, J=4.55 and 1.77 Hz).

Provenance & Evidence