Triphosgene → 4-(4-Fluorophenyl)oxazolidine-2,5-dione

HRID 625746Notes

Reaction equation

HRID 625746 reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]2[C:3](=[O:5])[O:4][C:14](=[O:16])[NH:1]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 98313(1)-4-Fluorophenylglycine

Product 1

HCID 866490494-(4-Fluorophenyl)oxazolidine-2,5-dioneYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-amino-2-(4-fluorophenyl)acetic acid (5 g, 29.5 mmol) in THF (50 mL) at 50° C. was added triphosgene (8.77 g, 29.5 mmol), then heating was continued for 3 h. The reaction mixture was then filtered and evaporated to a volume of about 10 mL, followed by addition of 150 mL of hexanes. The mixture was heated slightly, and then cooled to −20° C. for 1 h. The crude slurry was filtered to give 4-(4-fluorophenyl)oxazolidine-2,5-dione (5.03 g, 87%) which was used without further purification.

Workup

  1. temperatureheating
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated to a volume of about 10 mL
  4. additionfollowed by addition of 150 mL of hexanes
  5. temperatureThe mixture was heated slightly
  6. filtrationThe crude slurry was filtered

Sources & evidence

ORD record
ord-34b7cc5eb5c8410b8ef236993f76ade4
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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