Hydrochloric Acid → 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, 17.5 ml. of water and 12.5 ml. of ethanol. This mixture was heated to refluxing and a aqueous solution of 1.1 g. of hydroxylamine hydrochloride was added dropwise. When addition was complete the pH of the mixture was about 7.2. This was adjusted to pH about 6.3 using 10% aqueous hydrochloric acid. After 1 hour the pH was about 7.0 and was adjusted with 10% HCl to pH about 6.5. At the end of 2 hours the pH was about 6.8. At the end of 3 hours the pH was about 6.9. At 31/2 hours the pH was about 6.5. The reaction mixture was refluxed overnight and the following morning the pH was about 6.8. The reaction mixture was concentrated using the rotovapor and the solid material which precipitated was filtered off and dried. It weighed 1.3 g., had a melting point of about 103°-104° C., and was determined by vpc to contain 90.68% of 3-amino-5-(t-butyl)-isoxazole and 6.68% of 5-amino-3-(t-butyl)isoxazole. Yield: 65.9% of desired isomer.

1. customround bottom flask there was placed
2. temperatureThis mixture was heated
3. temperatureto refluxing
4. additionWhen addition
5. customAt the end of 2 hours
6. customAt the end of 3 hours
7. custom2 hours
8. temperatureThe reaction mixture was refluxed overnight
9. concentrationThe reaction mixture was concentrated
10. customthe solid material which precipitated
11. filtrationwas filtered off
12. customdried

ORD record

ord-68dcb4b46b4644ebb9e0d66f6d07ffe0

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04259501