Water → 2-Oxazolidinone, 5-(phenylmethyl)-

HRID 1600010Notes

Reaction equation

HRID 1600010 reaction equation
[O:1]1[CH2:10][CH:2]1[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O-][C:12]#[N:13].[K+].[OH2:15]>CN(C=O)C>[CH2:3]([CH:2]1[O:1][C:10](=[O:15])[NH:13][CH2:12]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 948262-(Phenylmethyl)oxiraneHCID 11378442Potassium cyanate

Product 1

HCID 30392712-Oxazolidinone, 5-(phenylmethyl)-Yield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Epoxypropylbenzene (60 g, 448 mmol) and potassium cyanate (70 g, 364 mmol) were refluxed in DMF (600 ml) and water (300 ml) for 4 hours. The solvent was evaporated in vacuo and water added. The aqueous was then extracted with ethyl acetate, dried (Mg SO4) and evaporated. Recrystallization from ethyl acetate gave the product (28.2 g, 36%) Mpt 106°-107° C. MS (EI) 177 (M+), 133, 86.

Workup

  1. customThe solvent was evaporated in vacuo and water
  2. additionadded
  3. extractionThe aqueous was then extracted with ethyl acetate
  4. dry with materialdried (Mg SO4)
  5. customevaporated
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-11419868bbaf415eba0f2b72783e68d7
Source dataset
uspto-grants-1998_04
Patent number
US05744466

Reaction notes

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