Hydrochloric Acid → 3-chloro-1-[2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propoxy]-3-methyl-2-nitrosobutane

Participants

Reaction Steps

To a cooled (0°-5° C.) stirred slurry of 1-[2-hydroxy-3-(2 -nitro-1H-imidazol-1-yl)propyl dimethylallyl ether (7.0 g, 0.0275 mol) in isoamyl nitrite (43 g, 50 mL, 0.042 mol) was added concentrated hydrochloric acid (2.5 mL, 0.03 mol) with stirring. The reaction mixture was maintained below 5° C. during the addition and stirred at 5° C. for an additional 2 hrs. The solid formed was stirred with cold ether-ethanol (3:1, 150 mL), filtered, and dried under vacuum. Yield: 5.8 g (67%). mp: 116°-117° C. dec. 1H NMR (DMSO) δ1.55 and 1.62 (s, 6H, CH3), 3.35 (m, 4H, CH2OCH2CHOH), 3.82 (m, 1H, CHOH), 4.1-4.52 (m, 2H, CHOHCH2N<), 5.3 (m, 1H, CHOH), 6.0 (dd, 1H, CHNO), 7.15 and 7.42 (s, 2H, imi H).

Provenance & Evidence