To a slurry of 2.25 grams (.025 moles) of carbohydrazide in 30 ml of methanol stirred by a magnetic stirrer in a 50 ml erlenmeyer flask was added 10.5 grams (.05 moles) of 1-t-butylazo-1-isocyanatocyclohexane (from Example XVIII). The carbohydrazide slowly went into solution over 1 hour. The reaction solution was allowed to stand overnight at room temperature. The next morning the solution was poured into 200 ml water and the product extracted with methylene chloride. The methylene chloride extract was washed with water, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure to leave a sticky solid. The sticky solid was redissolved in pentane and the pentane evaporated under reduced pressure to give a light yellow crystalline solid that weighed 12.0 grams (94% crude yield). The product did not melt sharply but began to decompose around 100° C. The infrared spectrum of the product contained a strong broad carbonyl band at 1660-1700 cm-1 and NH bands at 3280 -3370 cm-1 and the isocyanate band of the starting material was absent.
