Hydrochloric Acid → 3-(4-Fluorophenyl)-1,2-oxazol-5-amine

HRID 1156534Notes

Reaction equation

HRID 1156534 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[NH2:18][OH:19].Cl>O.C(O)C>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]2[CH:8]=[C:9]([NH2:10])[O:19][N:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 517045Sodium AcetateHCID 2783172p-Fluorobenzoylacetonitrile

Product 1

HCID 20603323-(4-Fluorophenyl)-1,2-oxazol-5-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(4-Fluorobenzoyl)acetonitrile (10 g., 0.063 mol) and 200 ml. of ethyl alcohol were placed in a 500 ml. 1-neck flask. To the reaction mixture was added in portionwise fashion a solution comprised of 24 g. of sodium acetate and 18.3 g. of hydroxylamine.HCl in 200 ml. of H2O. After refluxing for three days, the reaction mixture was cooled to room temperature. About half the solvent was removed and then an oily layer formed. The residue was extracted thoroughly in ether and then the combined ether extracts were washed in water, brine, and then dried over MgSO4. When the ether was removed orange crystals formed which were recrystallized from diethyl ether/hexane, m.p., 98°-99° C.

Workup

  1. additionTo the reaction mixture was added in portionwise fashion a solution
  2. temperatureAfter refluxing for three days
  3. customAbout half the solvent was removed
  4. customan oily layer formed
  5. extractionThe residue was extracted thoroughly in ether
  6. washthe combined ether extracts were washed in water
  7. dry with materialbrine, and then dried over MgSO4
  8. customWhen the ether was removed orange crystals
  9. customformed which
  10. customwere recrystallized from diethyl ether/hexane, m.p., 98°-99° C.

Sources & evidence

ORD record
ord-6befdf2529c44ccc84ba5a08fa46a0d2
Source dataset
uspto-grants-1982_06
Patent number
US04336264

Reaction notes

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