Cyanogen Bromide → HCID 10064427, compound

Participants

Reaction Steps

A solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide (0.50 g, 1.71 mmol) in dioxane (15 mL) is added to a solution of sodium bicarbonate (0.16 g, 1.88 mmol) in water (4 mL). Cyanogen bromide (0.20 g, 1.88 mmol) is then added in 4 equal portions at 1-minute intervals, and stirring is continued for 5 hours. The reaction mixture is diluted with ethyl acetate and sequentially washed with aqueous sodium bicarbonate, water, and brine. Drying the organic phase over magnesium sulfate and evaporation provides a solid which is crystallized from ethyl acetate/hexane followed by methanol/water to give 0.32 g (59%) of 4-[2-(5-amino-1,3,4-oxadiazol-2-yl)ethyl]-2,6-bis(1,1-dimethylethyl)phenol, mp 220.0°-221.0° C.

Provenance & Evidence