Phosgene → 5-Phenyloxazolidine-2,4-dione

HRID 544302Notes

Reaction equation

HRID 544302 reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.[OH:6][CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8](=[NH:12])[O:9]CC.O1CCCC1>C1(C)C=CC=CC=1>[C:13]1([CH:7]2[O:6][C:1](=[O:2])[NH:9][C:8]2=[O:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 12387918Ethyl 2-hydroxy-2-phenylethanimidate--hydrogen chloride (1/1)

Product 1

HCID 840425-Phenyloxazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the procedure of Example 3, except that a reaction time of 16 hours at room temperature was used following cold perfusion with phosgene, ethyl 1-hydroxy-1-phenylmethanecarboximidate hydrochloride (22 g., 0.102 mole) in 450 ml. of tetrahydrofuran was converted to toluene recrystallized 5-phenyloxazolidine-2,4-dione (10.5 g., m.p. 103°-105° C.).

Workup

  1. customexcept that a reaction time of 16 hours
  2. customat room temperature
  3. customrecrystallized 5-phenyloxazolidine-2,4-dione (10.5 g., m.p. 103°-105° C.)

Sources & evidence

ORD record
ord-709f2981513f418982411cfaa2b42b97
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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