Sodium Hydroxide → 5-Phenyl-1,2-oxazol-3-amine

HRID 1241596Notes

Reaction equation

HRID 1241596 reaction equation
[C:1]1([C:7]#[C:8][C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][OH:13].[OH-].[Na+]>CCO.O>[NH2:10][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:13][N:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 96382Propiolonitrile, phenyl-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 36207925-Phenyl-1,2-oxazol-3-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-phenyl-2-propyne-nitrile (1.27 g, 0.01 mol, Step A) in EtOH (20 mL) was added at RT hydroxylamine hydrochloride (3.5 g, 0.05 mol) followed by 10% NaOH (28 mL). The exothermic reaction was stirred at RT 24 h, then diluted with H2O. The resulting precipitate was filtered off, washed with H2O and dried over P2O5 to afford 3-amino-5-phenylisoxazole as a white crystalline solid.

Workup

  1. customThe exothermic reaction
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with H2O
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-2e390789c1c84e09a7cf468793ca3451
Source dataset
uspto-grants-2006_10
Patent number
US07115617B2

Reaction notes

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