Water → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-
Reaction equation
[C:1]([CH2:7][C:8]#[N:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].O.Cl.[NH2:14]O>C(O)C>[NH2:9][C:8]1[CH:7]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[O:6][N:14]=1Participants
Procedure
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 and the pH was determined to be about 8.9. Then an aqueous solution of 1.0 g. of hydroxylamine hydrochloride was slowly added. At the end of the addition the pH was about 6.3. The pH of the reaction mixture was adjusted to about 6.5. After 1 hour, the pH was about 6.3 and was again adjusted to about 6.5. After 2 hours the pH was observed to be about 7.0 and was again adjusted to pH about 6.5. At 3 hours and again at 4 hours, the pH was determined to be about 6.5. The reaction mixture was allowed to reflux overnight and the following morning the pH was determined to be about 6.1. The ethanol was removed using a rotovapor and a yellow solid precipitated. This solid was filtered off and dried. It weighed 1.1 g. and it was determined by vpc to contain 94.2% of 3-amino-5-(t-butyl)isoxazole and 3.7% of 5-amino-3-(t-butyl)isoxazole. The product had a melting point of about 103°-105° C. Yield: 73.6% of desired isomer.
Workup
- customround bottom flask there was placed
- temperatureThis mixture was heated
- temperatureto reflux
- additionAt the end of the addition the pH was about 6.3
- waitAfter 2 hours the pH was observed
- waitAt 3 hours
- waitagain at 4 hours
- temperatureto reflux overnight
- customThe ethanol was removed
- customa yellow solid precipitated
- filtrationThis solid was filtered off
- customdried
Sources & evidence
- ORD record
- ord-2c6f58409e834337b6f44422c58d31ed
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04259501
Reaction notes
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