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

HRID 343915Notes

Reaction equation

HRID 343915 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 anaylsis 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-b0c7a99384744d108579af2ebabd9c3f
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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