Hydrochloric Acid → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

Participants

Reaction Steps

In a 1 l. round bottom 3-neck flask there was placed 30 g. of pivalyl acetonitrile, 12.8 g. of sodium hydroxide, 394 ml. of water, and 281 ml. of ethanol. This mixture was heated to refluxing and there was added thereto over a period of about 10 minutes an aqueous solution of 22.2 g. of hydroxylamine hydrochloride. The pH of the reaction mixture after addition was complete was about 6.4. After 30 minutes the pH was determined to be about 6.5. After 11/2 hours the pH was about 6.8, and after 2 hours the pH was about 7.0. The pH was adjusted to about 6.2 using concentrated aqueous hydrochloric acid. After another 3 hours the pH was about 6.6. The reaction mixture was refluxed overnight and at the end of 22 hours of reaction time the pH was about 7.3. The reaction mixture was cooled and ethanol removed in vacuo. The solid which separated was filtered off and dried. It weighed 18.9 g., had a melting point of about 103°-105° C., and was determined by vpc to contain 91.2% of 3-amino-5-(t-butyl)isoxazole and 5.2% of 5-amino-3-(t-butyl)isoxazole. Yield: 56% of desired isomer.

Provenance & Evidence