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

In a 100 ml. round bottom flask there was placed 2 g. of pivalyl acetonitrile, 0.64 g. of sodium hydroxide, 35 ml. of water, and 25 ml. of ethanol. This mixture was heated to reflux. The pH of the mixture was determined to be about 8.6. Then 1.1 g. of hydroxylamine hydrochloride in 15 ml. of water was added dropwise. At the end of the addition the pH of the reaction mixture was about 5.1. The pH of the reaction mixture was adjusted to about 7.0. After 1 hour the pH was determined to be about 7.6 and was adjusted back to about 7.0. After 2 hours the pH was determined to be about 6.9 and was readjusted to about 7.0. After 3 hours the pH was determined to be about 7.5 and was adjusted to about 7.0. After 4 hours the pH was determined to be about 6.8 and was readjusted to about 7.0. The reaction mixture was allowed to reflux overnight and the following morning the pH was determined to be about 6.3 and was readjusted to about 7.0. The ethanol solvent was stripped using a rotovapor and a yellow solid precipitated. The solid was filtered off and dried. The solid weighed 1.1 g. and had a melting point of about 101°-104° C. It was determined by vpc to contain 92.6% of 3-amino-5-(t-butyl)isoxazole and 4% of 5-amino-3-(t-butyl)isoxazole. Yield: 72.9% of desired isomer.

1. customround bottom flask there was placed
2. temperatureThis mixture was heated to reflux
3. additionAt the end of the addition the pH of the reaction mixture
4. waitAfter 2 hours the pH was determined
5. waitAfter 3 hours the pH was determined
6. waitAfter 4 hours the pH was determined
7. temperatureto reflux overnight
8. customa yellow solid precipitated
9. filtrationThe solid was filtered off
10. customdried

ORD record

ord-9c493092b0e54308b35daff60b284786

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04259501