Hydrochloric Acid → HCID 57781136, compound

Participants

Reaction Conditions

Reaction Steps

Dioxane (22 mL) and 1M aqueous KOH (22 mL, 22 mmol) are added to N,N-diethyl-2-[2-hydroxy-1-(5-iodo-imidazol-1-yl)-2-methyl-propyl]-benzamide (1.65 g) and the mixture is heated to 60° C. After 13.5 h, the mixture is cooled to 0° C. and acidified to pH=1 with conc. HCl. The mixture is heated to 60° C. After 24 h, the mixture is diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate and filtered through a cotton plug. Concentration in vacuo gave an orange solid, which is purified by silica gel flash chromatography (methylene chloride-methanol, 49:1) to give a crystalline yellow solid; MS (ESI) m/z 369.0 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (s, 3 H), 1.57 (s, 3 H), 5.39 (s, 1 H), 7.19 (s, 1 H), 7.28 (br. d, J=7.6 Hz, 1 H), 7.39 (s, 1 H), 7.59 (td, J=7.6, 1.3 Hz, 1 H), 7.66 (td, J=7.6, 1.3 Hz, 1H), 8.27 (dd, J=7.6, 1.4 Hz, 1 H).

Provenance & Evidence