Cl.[NH2:2][OH:3].[OH-].[Na+].[C:6]([N:10]=[N:11][C:12]([C:15]#[N:16])([CH3:14])[CH3:13])([CH3:9])([CH3:8])[CH3:7].O>CO.CCCCC>[C:6]([N:10]=[N:11][C:12]([CH3:14])([CH3:13])[C:15](=[N:2][OH:3])[NH2:16])([CH3:9])([CH3:7])[CH3:8]
To a mixture of 8.35 grams (0.12 moles) of hydroxylamine hydrochloride and 9.6 grams (0.12 moles) of 50% NaOH in 110 ml of 90% aqueous methanol in a 250 ml round bottom flask equipped with a magnetic stirrer and condenser was added 15.3 grams (0.1 moles) of 2-t-butylazo-2-cyanopropane (from Example I). The mixture was stirred for 72 hours at room temperature, poured into 400 ml of water and extracted with 100 ml of methylene chloride, the organic layer separated, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure leaving a soft solid. The residue was slurried in 100 ml of pentane to remove any unreacted 2-t-butylazo-2-cyanopropane, filtered and the filter cake air dried. The yield was 12.5 grams (67% yield) of a white solid having a melting point of 105°-109°C (dec.). The infrared spectrum of the product was in agreement with the structure of the desired amidoxime.
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