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

HRID 615525Notes

Reaction equation

HRID 615525 reaction equation
Cl.[NH2:2]O.[C:4]([CH2:10][C:11]#[N:12])(=[O:9])[C:5]([CH3:8])([CH3:7])[CH3:6].Cl.[OH-].[Na+]>O.C(O)C>[NH2:12][C:11]1[CH:10]=[C:4]([C:5]([CH3:8])([CH3:7])[CH3:6])[O:9][N:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 41.5 g of hydroxylamine hydrochloride in 136 ml of water was added drop-by-drop over a 10-minute period to a stirred, refluxing mixture of 56.1 g of pivaloylacetonitrile (British Pat. No. 2,014,992), 700 ml of water and 525 ml of ethanol. The mixture was held under those conditions for 7 hours, the pH of the mixture being periodically adjusted to 6.5 by the addition of either hydrogen chloride or aqueous sodium hydroxide solution, as required. Then the solvent ethanol was evaporated in a rotary evaporator, and the residual liquid was dried (MgSO4), dissolved in 200 ml of hexane and chilled. Filtration gave 3-amino-5-(1,1-dimethylethyl)-isoxazole (1A), a yellow solid, m.p.: 107°-109° C.

Workup

  1. temperaturerefluxing
  2. customThen the solvent ethanol was evaporated in a rotary evaporator
  3. dry with materialthe residual liquid was dried (MgSO4)
  4. dissolutiondissolved in 200 ml of hexane
  5. temperaturechilled
  6. filtrationFiltration

Sources & evidence

ORD record
ord-e7662fdc7bb641e68691b8ba9ae146c6
Source dataset
uspto-grants-1985_02
Patent number
US04500345

Reaction notes

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