Phosgene → 3-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione

HRID 648290Notes

Reaction equation

HRID 648290 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[C:16](Cl)(Cl)=[O:17]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([CH:10]([CH3:12])[CH3:11])[C:13](=[O:15])[O:14][C:16]2=[O:17])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6371Phosgene3×HCID 13796078N-(p-chlorophenyl)valine

Product 1

HCID 132294943-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4.9 g of N-(4-chlorophenyl)valine (0.0215 mole) in 50 ml of 1,4-dioxane is slowly passed a stream of phosgene gas as the solution is stirred. Cooling is applied to keep the solution at RT. When the solution is saturated with phosgene, the phosgene is shut off and the mixture is allowed to stir under nitrogen at RT. After 45 hr, about two-thirds of the dioxane is removed by distilling at aspirator pressure. The residue is diluted with hexane, then allowed to crystallize overnight at RT. The solid is collected by filtration and washed with hexane, with care being taken to minimize exposure to air. The solid is dried in vacuo to yield 3-(4-chlorophenyl)-4-isopropyloxazolidine-2,5-dione, m.p. 137°-138°.

Workup

  1. temperatureCooling
  2. customat RT
  3. stirringto stir under nitrogen at RT
  4. customabout two-thirds of the dioxane is removed
  5. distillationby distilling at aspirator pressure
  6. additionThe residue is diluted with hexane
  7. customto crystallize overnight at RT
  8. filtrationThe solid is collected by filtration
  9. washwashed with hexane, with care
  10. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-d087cba4ca234d18b81036e8701c9294
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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