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

HRID 1632117Notes

Reaction equation

HRID 1632117 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 patent 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, the residual liquid was dried (MgSO4), and placed in 200 ml of hexane and chilled. Filtration and fractional crystallization of the solid gave 3-amino-5-(tertiary-butyl)-1,2-oxazole (1A), a yellow solid, m.p.: 107°-109° C. A second fraction was 5-amino-3-(tertiary-butyl)-1,2-oxazole (1B), a solid, m.p.: 89°-90° 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. temperaturechilled
  5. filtrationFiltration and fractional crystallization of the solid

Sources & evidence

ORD record
ord-4cbabb1d4b13450888b51045c46083fc
Source dataset
uspto-grants-1984_10
Patent number
US04474598

Reaction notes

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