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

HRID 128438Notes

Reaction equation

HRID 128438 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]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-Yield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customround bottom 3-neck flask was placed
  2. temperatureThis mixture was heated
  3. temperatureto reflux
  4. additionThe pH at the end of the addition
  5. waitAfter 2 hours the pH was determined
  6. waitAfter 3 hours the pH was determined
  7. temperatureThe following morning after the reaction mixture had refluxed overnight the pH was about 7.2
  8. customThe ethanol was removed in vacuo
  9. customThe solid which separated
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-e66542795a204293b7e95df2791077eb
Source dataset
uspto-grants-1981_03
Patent number
US04259501

Reaction notes

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