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

HRID 1608996Notes

Reaction equation

HRID 1608996 reaction equation
[OH-].[K+].Cl.[NH2:4][CH2:5][CH:6]([OH:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15](Cl)(Cl)=[O:16]>O.C1(C)C=CC=CC=1>[CH2:7]([CH:6]1[O:14][C:15](=[O:16])[NH:4][CH2:5]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 177498841-Amino-3-phenylpropan-2-ol hydrochloride

Product 1

HCID 30392712-Oxazolidinone, 5-(phenylmethyl)-Yield 45.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of KOH (9.4 g) in water (85 ml) was added to a stirred solution of the product from step (b) (5.1 g) in toluene (150 ml) at 0° C. A solution of phosgene (9.8 g) in toluene (78.4 ml 12.5% w/v) was added dropwise over 15 minutes and the mixture brought to room temperature, then stirred overnight. The aqueous phase was separated and extracted with ethyl acetate. The combined extracts were evaporated in vacuo to give the desired product as a white solid (2.2 g), mp 106°-108° C. Elemental analysis was consistent with the proposed structure.

Workup

  1. custombrought to room temperature
  2. customThe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. customThe combined extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-1ff1a925fa3d4362adea6f779d5ec14d
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

Loading…