Dimethylformamide → (5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone

HRID 54869

Reaction equation

HRID 54869 reaction equation
[CH2:1]1[O:9][C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=O)=[CH:14][CH:13]=1.CN(C)C=[O:24]>[Cl-].[Li+]>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][C@@H:2]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[O:9][C:1]2=[O:24])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 794431-Isocyanato-4-methoxybenzeneHCID 114705(+)-Styrene oxide

Product 1

HCID 53894593(5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinoneYield 53.8%

Reagents, catalysts & solvents 1

HCID 433294Lithium ChlorideCatalyst

Procedure

3.50 g (29.1 mM) of (R)-(+)-styrene oxide, 0.035 g of lithium chloride and 14 ml of N,N-dimethylformamide (DMF) were placed in a 50 ml-three necked flask. Under refluxing and stirring in nitrogen atmosphere, a solution of 4.38 g (29.4 mM) of 4-methoxyphenyl isocyanate in 3.5 ml of DMF was added dropwise to the mixture in 40 minutes, followed by refluxing for 40 minutes under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and recrystallized from methanol. The resultant crystal was purified by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1) and recrystallized from a toluene/methanol mixture solvent to obtain 4.22 g of (5R)-3-(4-methoxyphenyl)-5-phenyl-2-oxazolidinone (Yield: 53.8%). This compound showed the following phase transition series.

Workup

  1. temperatureUnder refluxing
  2. temperatureby refluxing for 40 minutes
  3. stirringunder stirring
  4. customAfter the reaction
  5. customto precipitate a crystal
  6. filtrationThe crystal was recovered by filtration
  7. washwashed with water
  8. customrecrystallized from methanol
  9. customThe resultant crystal was purified by silica gel column chromatography (eluent: toluene/ethyl acetate =100/1)
  10. customrecrystallized from a toluene/methanol mixture solvent

Sources & evidence

ORD record
ord-533bfd7a4c5d4057b5b495e5fffe3c3b
Source dataset
uspto-grants-1997_04
Patent number
US05624600

Linked notes

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