Methanol → 3-(4-Nitro-benzyl)-oxazolidin-2-one

HRID 44271Notes

Reaction equation

HRID 44271 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.CO>C1COCC1.C1COCC1.CN(C=O)C.O>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:8])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

8

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 739492-Oxazolidinone

Product 1

HCID 666364983-(4-Nitro-benzyl)-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% as a dispersion in oil, 0.34 mol) in anhydrous THF (60 ml) at 0° C. there is added, dropwise, a solution of oxazolidin-2-one (0.31 mol) under an inert atmosphere. The reaction mixture is brought to ambient temperature and stirred for one hour. A solution of 1-bromomethyl-4-nitro-benzene (0.35 mol) in a mixture of THF/DMF (10/1) (250 ml) is added dropwise at 0° C. The reaction mixture is then stirred overnight at ambient temperature. The solution is then cooled to 0° C. There are then added, in succession, 20 ml of MeOH and 20 ml of water. The suspension obtained is then concentrated and then poured into 500 ml of water. The solution is then extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, is dried over sodium sulphate and is then filtered. The filtrate obtained is concentrated and the solid formed is filtered off, washed with ethyl ether and then dried in vacuo to yield the title product, which is used directly in the next Step.

Workup

  1. additionthere is added
  2. customis brought to ambient temperature
  3. additionis added dropwise at 0° C
  4. stirringThe reaction mixture is then stirred overnight at ambient temperature
  5. customThe suspension obtained
  6. concentrationis then concentrated
  7. additionpoured into 500 ml of water
  8. extractionThe solution is then extracted with DCM
  9. customThe organic phase obtained
  10. washis washed with water and with saturated aqueous NaCl solution
  11. dry with materialis dried over sodium sulphate
  12. filtrationis then filtered
  13. customThe filtrate obtained
  14. concentrationis concentrated
  15. customthe solid formed
  16. filtrationis filtered off
  17. washwashed with ethyl ether
  18. customdried in vacuo

Sources & evidence

ORD record
ord-dd6af6ed340c426398f6d6f42ba764c0
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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