Phosgene → HCID 13092013, compound

HRID 434822Notes

Reaction equation

HRID 434822 reaction equation
[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[C:3](=[NH:7])[O:4]CC.C(N(CC)CC)C.[C:25](Cl)(Cl)=[O:26]>O1CCCC1>[F:17][C:14]([F:15])([F:16])[C:10]1[CH:9]=[C:8]([CH:2]2[O:1][C:25](=[O:26])[NH:4][C:3]2=[O:7])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 13599060HCID 13599060, compound

Product 1

HCID 13092013HCID 13092013, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-hydroxy-1-(3-trifluoromethylphenyl)methane carboximidate (9.5 g., 0.038 mole) was dissolved in 500 ml. of tetrahydrofuran and cooled to 0°-5° C. Triethylamine (7.68 g., 0.076 mole) was added and the solution perfused with phosgene for 35 minutes at 0°-5° C. After stirring for 1.5 hours, isolation and recrystallization according to Example 3 gave 5-(3-trifluoromethylphenyl)oxazolidine-2,4-dione (6.4 g., 69%, m.p. 93°-96° C.). A second recrystallization from toluene gave purified product (4.9 g., 53% over-all; m.p. 97°-99° C., m/e 245).

Workup

  1. customisolation and recrystallization

Sources & evidence

ORD record
ord-fd0d3d8764fa477482aa3716e9e11f77
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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