Diethyl Carbonate → 3-(4-Bromo-3-methyl-phenyl)-oxazolidin-2-one

HRID 1754973Notes

Reaction equation

HRID 1754973 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.C[O-].[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]CCO)=[CH:15][C:14]=1[CH3:23].[Cl-].[NH4+]>CO>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:7][CH2:6][O:5][C:1]2=[O:8])=[CH:15][C:14]=1[CH3:23]

Participants

6

Reactant 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 285749422-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol

Product 1

HCID 668178513-(4-Bromo-3-methyl-phenyl)-oxazolidin-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
110 °C

Procedure

Diethyl carbonate (18 ml) and a 28% solution of sodium methoxide in methanol (1.1 ml, 5.70 mmol) were added to 2-(4-bromo-3-methyl-phenylamino)-ethanol (1.21 g, 5.27 mmol), and the mixture was heated with stirring at 110° C. for 15 hours. Further, methanol (16 ml) was added to the reaction solution, and the mixture was heated with stirring at 110° C. for one hour. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic phase was sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was triturated with hexane to give 3-(4-bromo-3-methyl-phenyl)-oxazolidin-2-one (989 mg, 73%).

Workup

  1. temperaturethe mixture was heated
  2. temperaturethe mixture was heated
  3. stirringwith stirring at 110° C. for one hour
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic phase was sequentially washed with water and saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-8eb0e548714c46228b713a514b5f830f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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