Lithium Chloride → 3-(4-Octylphenyl)-5-(4-hexylphenyl)-2-oxazolidinone

HRID 54875Notes

Reaction equation

HRID 54875 reaction equation
[Cl-].[Li+].C(O[C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1)CCCCCCC.[CH2:21]([C:27]1[CH:35]=[CH:34][C:30]([CH:31]2[O:33][CH2:32]2)=[CH:29][CH:28]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C=O)C>[CH2:28]([C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:32][CH:31]([C:30]3[CH:34]=[CH:35][C:27]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=3)[O:33][C:19]2=[O:20])=[CH:16][CH:17]=1)[CH2:27][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 27694194-(Octyloxy)phenyl isocyanateHCID 19956695HCID 19956695, compound

Product 1

HCID 199566923-(4-Octylphenyl)-5-(4-hexylphenyl)-2-oxazolidinoneYield 14.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4 mg of lithium chloride and 1.0 ml of DMF were placed in a 20 ml-three necked flask. Under refluxing and stirring in nitrogen atmosphere, a solution of 0.97 g (3.92 mM) of 4-octyloxyphenyl isocyanate and 0.80 g (3.92 mM) of (-)-4-hexylstyrene oxide in 1.8 ml of DMF was added dropwise to the mixture in 5 minutes, followed by refluxing for 5 minutes under stirring. After the reaction, the reaction mixture was cooled to room temperature and poured into ice water to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in a toluene-ethyl acetate mixture solvent, followed by drying with anhydrous sodium sulfate and evaporation under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography and recrystallized from an acetone/methanol mixture solvent to obtain 0.25 g of optically active 3-(4-octylphenyl)-5-(4-hexylphenyl)-2-oxazolidinone (Yield: 14.1%). This compound showed the following phase transition series.

Workup

  1. temperatureUnder refluxing
  2. temperatureby refluxing for 5 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. dissolutiondissolved in a toluene-ethyl acetate mixture solvent
  9. dry with materialby drying with anhydrous sodium sulfate and evaporation under reduced pressure
  10. customto obtain a residue
  11. customThe residue was purified by silica gel column chromatography
  12. customrecrystallized from an acetone/methanol mixture solvent

Sources & evidence

ORD record
ord-722f070fb0934eb5affef32660ed69ff
Source dataset
uspto-grants-1997_04
Patent number
US05624600

Reaction notes

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