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

HRID 1098553Notes

Reaction equation

HRID 1098553 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[C:6]([CH2:12][C:13]#[N:14])(=O)[C:7]([CH3:10])([CH3:9])[CH3:8]>>[C:7]([C:6]1[CH:12]=[C:13]([NH2:14])[O:1][N:4]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 3

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

Product 1

HCID 20956943-Tert-butyl-1,2-oxazol-5-amineYield 76%

Conditions

Temperature
50 °C

Procedure

To an aqueous solution of sodium hydroxide solution (40.00 g, 1 mol, in 200 ml of water) was added hydroxylamine hydrochloride (24.00 g, 346 mmol) and pivaloylacetonitrile (40.00 g, 320 mmol). The resulting solution was stirred at 50° C. for 3 hrs. The reaction mixture cooled and the resultant white crystalline solid filtered, washed with water and dried to provide 3-t-butylisoxazol-5-amine as a white crystalline solid (34 g, yield 76% yield). 1H NMR (DMSO-d6) δ 6.41 (brs, 2H), 4.85 (s, 1H), 1.18 (s, 9H): LC-MS (ES, m/z, M+H) 141.3.

Workup

  1. temperatureThe reaction mixture cooled
  2. filtrationthe resultant white crystalline solid filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f8e00af30de3403789464712608fb85c
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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