Cyanogen Bromide → HCID 19900660, compound

Participants

Reaction Steps

A solution of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanoic acid hydrazide (0.50 g, 1.54 mmol) in dioxane (15 mL) is added to a solution of sodium bicarbonate (0.14 g, 1.62 mmol) in water (4 mL). Cyanogen bromide (0.17 g, 1.62 mmol) is added in four 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 to give 0.42 g (78%) of 4-[[2-(5-amino-1,3,4-oxadiazol-2-yl)ethyl]thio]-2,6-bis(1,1-dimethylethyl)phenol, mp 172.0°-174.0° C.

Provenance & Evidence