Hydrochloric Acid → 5-Phenyl-1,2-oxazol-3-amine

HRID 1521747Notes

Reaction equation

HRID 1521747 reaction equation
C(O)C.O[NH:5][C:6](=[NH:19])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)OCC[O:9]1.Cl>O>[C:13]1([C:8]2[O:9][N:5]=[C:6]([NH2:19])[CH:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178510736HCID 178510736, compound

Product 1

HCID 36207925-Phenyl-1,2-oxazol-3-amineYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Ethanol (125 mL) and H2O (25 mL) are added to N-hydroxy-2-(2-phenyl-1,3-dioxolan-2-yl)ethanimidamide (7 g, 32 mmol). The pH is adjusted to 1 with the addition concentrated HCl and the reaction mixture is heated at 90° C. for 2 h. The solvent is evaporated to dryness and the resulting residue is neutralized using phosphate buffer. The mixture is extracted with ethyl acetate and the combined organic phases are dried (Na2SO4) and concentrated in vacuo. The crude residue is purified over neutral alumina eluting with 30% ethyl acetate/hexane to afford the title compound as an off-white solid (1.7 g, 34%).

Workup

  1. customThe solvent is evaporated to dryness
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is purified over neutral alumina eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c086c8829e14a69b1bd454afc5ffe52
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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