Water → HCID 20368600, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.5 grams (0.0264 moles) of 2-t-butylazo-2-(β-hydroxyethylthio)-4-methylpentane and 2.5 grams (.031 moles) of pyridine in 50 ml of pentane in a beaker was added 5.75 grams (.025 moles) of 4-t-butylazo-4-cyanovaleryl chloride dropwise while holding the reaction temperature at 25° ± 2° C. After the addition was complete, the reaction was stirred an additional 1/2 hour at 25° C, 50 ml of water added and the pentane layer separated. The pentane layer was successively washed with 25 ml of 10% HCl, 25 ml of water and 25 ml of 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave a viscous tan liquid weighing 7.3 grams (66% yield). The product was purified by chromatographing it over alumina and eluting it with pentane. Evaporation of the pentane left a yellow viscous liquid whose infrared spectrum was in agreement with the structure of the desired product.

Provenance & Evidence