Water → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

Participants

Reaction Steps

In a 100 ml. round bottom 3-neck flask was placed 2 g. of pivalyl acetonitrile, 0.64 g. of sodium hydroxide, 35 ml. of water and 12.5 ml. of ethanol. This mixture was heated to reflux and an aqueous solution of 1.1 g. of hydroxylamine hydrochloride was added. The pH at the end of the addition was about 6.0. After 1 hour the pH was determined to be about 6.3. After 2 hours the pH was determined to be about 6.7. After 3 hours the pH was determined to be about 6.5. The following morning after the reaction mixture had refluxed overnight the pH was about 7.2. The ethanol was removed in vacuo using the rotovapor. The solid which separated was filtered off and dried. It had a melting point of 105°-106° C., and weighed 1.1 g. It was determined by vpc that the product contained 92.49% of 3-amino-5-(t-butyl)isoxazole and 4.67% of 5-amino- 3-(t-butyl)isoxazole. Yield: 60.7% of desired isomer.

Provenance & Evidence