Dimethylformamide → 3-Benzyl-1,3-oxazolidin-2-one

HRID 1194492Notes

Reaction equation

HRID 1194492 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].CN(C=O)C.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH2:14][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:8])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 739492-Oxazolidinone

Product 1

HCID 104875283-Benzyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cold (ice-bath) suspension of sodium hydride (0.55 mole, hexane washed) in 100 mL of dry THF was stirred under a nitrogen atmosphere while a solution of 2-oxazolidinone in 500 mL of 10:1 THF:DMF was added dropwise. The resulting gray suspension was warmed to room temperature and stirred for 24 hour. Benzyl bromide (66 mL, 0.056 mole) was added to the resulting white suspension and stirred at ambient temperature 24 hour. The reaction was quenched by careful addition of 26 mL water and the resulting mixture was concentrated and poured into 500 mL of water. After extraction with methylene chloride, the combined extracts were washed with water and brine and dried over magnesium sulfate. Concentration in vacuo afforded 104 g of a yellow oil which was purified by Kugelrohr distillation (bp 100°/0.1 mm) to give 81 g (92% yield) of the product as a colorless liquid which solidified on standing at room temperature to a colorless solid, m.p. 76°-78°.

Workup

  1. stirringstirred at ambient temperature 24 hour
  2. customThe reaction was quenched by careful addition of 26 mL water
  3. concentrationthe resulting mixture was concentrated
  4. additionpoured into 500 mL of water
  5. extractionAfter extraction with methylene chloride
  6. washthe combined extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-8a317f9e2b9a4988854861cca5be00cb
Source dataset
uspto-grants-1989_03
Patent number
US04814455

Reaction notes

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