Water → (E)-1-tert-Butyl-2-(2-isothiocyanato-4-methylpentan-2-yl)diazene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 26.1 grams (0.3 moles) of sodium thiocyanate in 150 ml of 75% aqueous isopropanol in a 500 ml erlenmeyer flask, cooled to 5° C., was added 61.2 grams (0.3 moles) of 2-t-butylazo- 2-chloro-4-methylpentane holding the reaction temperature at 10°-20° C. After the addition was complete, the reaction mixture was stirred an additional two hours at 30° C., poured into 300 ml water and the product extracted with 200 ml pentane. The pentane extract was washed with water, 10% NaHCO3 solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 55.7 grams (80% crude yield) of a yellow liquid. The product had a strong broad band at 1980- 2080 cm-1 in its infrared spectrum which is indicative of the isothiocyano band.

Provenance & Evidence