Sodium Hydroxide → 3-Tert-butyl-1,2-oxazol-5-amine

HRID 469719Notes

Reaction equation

HRID 469719 reaction equation
S(O)(O)(=O)=O.[NH2:6][OH:7].[CH3:8][C:9]([CH3:16])([CH3:15])[C:10](=O)[CH2:11][C:12]#[N:13].[OH-].[Na+]>O>[C:9]([C:10]1[CH:11]=[C:12]([NH2:13])[O:7][N:6]=1)([CH3:16])([CH3:15])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 20956943-Tert-butyl-1,2-oxazol-5-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydroxylamine sulfate (27.575 g, 0.168 mol) is added to a stirred solution of 4,4-dimethyl-3-oxopentanenitrile (20 g; 0.160 mol) and sodium hydroxide (26.24 g; 0.656 mol) in water (160 mL). The mixture is heated at reflux for 2 hours, then allowed to cool to room temperature and extracted with methylene chloride. The combined organics are washed with water, dried (Na2SO4), filtered and concentrated in vacuo to afford title compound as a white solid. ESI m/z 141 [M+H]+

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with methylene chloride
  4. washThe combined organics are washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c80938b35b143329e5500cc78edee3a
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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