Chlorosuccinimide → Ethyl 5-chloro-2-phenyloxazole-4-carboxylate

HRID 2236173Notes

Reaction equation

HRID 2236173 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:9][CH:10]=1)=[O:5])[CH3:2].[Cl:17]N1C(=O)CCC1=O>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:9][C:10]=1[Cl:17])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 571056Ethyl 2-phenyl-1,3-oxazole-4-carboxylate

Product 1

HCID 67537623Ethyl 5-chloro-2-phenyloxazole-4-carboxylateYield 37.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

Mixture of 2-phenyl-oxazole-4-carboxylic acid ethyl ester (217 mg, 1 mmol), 1-chloro-pyrrolidine-2,5-dione (400 mg, 3 mmol) and two drops of sulfuric acid in chloroform (10 mL) was heated at 90 degrees for overnight. After the reaction was complete, solvent was evaporated. To the residue, water was added, and then the mixture was extracted with ethyl acetate twice. The organic layers were collected, combined, washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck silica gel 60, 230-400 mesh, 5-40% ethyl acetate in hexane for 30 min) gave 5-chloro-2-phenyl-oxazole-4-carboxylic acid ethyl ester (95 mg, 37%) as a white solid. LCMS calcd for C12H10ClNO3 (m/e) 251, obsd 252 (M+H).

Workup

  1. temperaturewas heated at 90 degrees for overnight
  2. customsolvent was evaporated
  3. additionTo the residue, water was added
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. customThe organic layers were collected
  6. washwashed with saturated sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c38f396e6def4bf5836fc95da9ebe164
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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