Hydroxyamine hydrochloride → 3-(3-(Trifluoromethyl)phenyl)-1,2-oxazol-5-amine

HRID 2059227Notes

Reaction equation

HRID 2059227 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([CH2:8][C:9]#[N:10])=O.C([O-])(=O)C.[Na+].Cl.[NH2:22][OH:23]>C(O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:6]2[CH:8]=[C:9]([NH2:10])[O:23][N:22]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5203043-(Trifluoromethyl)benzoylacetonitrile

Product 1

HCID 130355443-(3-(Trifluoromethyl)phenyl)-1,2-oxazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(Trifluoromethyl)benzoylacetonitrile (3.8 grams) and 125 ml. ethanol were placed in a 500 ml. flask. The solution was treated with sodium acetate (12 grams) and hydroxylamine.hydrochloride (9 grams in 125 ml. water) and then heated to reflux for two hours. After cooling to room temperature, the ethanol was removed and the residue extracted with ether. The ether extracts were then washed with water, brine, and dried with MgSO4. The solid residue obtained was recrystallized from an ethanol/water solution, m.p. 89°-90° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for two hours
  3. customthe ethanol was removed
  4. extractionthe residue extracted with ether
  5. washThe ether extracts were then washed with water, brine
  6. dry with materialdried with MgSO4
  7. customThe solid residue obtained
  8. customwas recrystallized from an ethanol/water solution, m.p. 89°-90° C.

Sources & evidence

ORD record
ord-7523057963bb400c8ce725c409847f9a
Source dataset
uspto-grants-1982_03
Patent number
US04322429

Reaction notes

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