Phosphorus oxychloride → Ethyl 5-(3-chlorophenyl)oxazole-2-carboxylate

HRID 2301879Notes

Reaction equation

HRID 2301879 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][NH:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)Cl>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:18][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 85809577Ethyl [[2-(3-Chlorophenyl)-2-oxoethyl]amino](oxo)acetate

Product 1

HCID 22350710Ethyl 5-(3-chlorophenyl)oxazole-2-carboxylateYield 51.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the product from Step 79b (1.28 g, 4.70 mmol, 1 eq), benzene (8 mL), and POCl3 (2.0 mL, 21 mmol) is heated under reflux for 65 h and cooled. The mixture is then evaporated and extracted between CHCl3 and water. The organic layer is separated, dried over MgSO4, filtered, and evaporated. The residue is crystallized from EtOH to give the title product (0.61 g, 51%). MS (ESI) for C12H10ClNO3 m/z 252 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 65 h
  3. temperaturecooled
  4. customThe mixture is then evaporated
  5. extractionextracted between CHCl3 and water
  6. customThe organic layer is separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from EtOH

Sources & evidence

ORD record
ord-761f6b695d6441f481f71c097cc66d29
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

Loading…