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

HRID 128985Notes

Reaction equation

HRID 128985 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-dfd18cbba70d42b2b943688122152bd3
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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