Dimethylformamide → Carbamic acid, octyl ester

Participants

Reaction Steps

To a heterogeneous mixture of 1-(2'-hydroxybutyl)-2,4-dinitroimidazole (500 mg, 2.17 mmol, Eur. J. Med. Chem. 24:631-633 (1989)) and 258 mg (2.60 mmol) of CuI in 10 mL of dry DMF was added 767 μL (4.34 mmol) of octyl isocyanate. The mixture was stirred for 2 h, diluted with 40 mL of ethyl ether and the organic solution was washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (hexane:ethyl acetate, 6:1) to give 502 mg (60%) of n-octyl carbamate. 1H NMR (CDCl3) δ 0.86 (t, 3H), 1.11 (t, 3H), 1.28 (m, 10H), 1.40 (m, 2H), 1.75 (m, 2H), 3.05 (m, 2H), 4.42 (q, 1H), 4.75 (t, 1H), 4.90 (q, 1H), 5.10 (m, 1H), 7.88 (s, 1H); 13C NMR (CDCl3) δ 9.32, 14.01, 22.54, 25.10, 26.54, 29.06, 29.63, 31.69, 40.04, 41.08, 54.28, 72.65, 124.14, 155.20; MS 386 (M+)

Provenance & Evidence