Ethanol → HCID 13093548, compound

HRID 434853Notes

Reaction equation

HRID 434853 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[O:15][C:14](=S)[NH:13][C:12]1=[O:17].C([OH:20])C.OO>C(Cl)(Cl)Cl.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[O:15][C:14](=[O:20])[NH:13][C:12]1=[O:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 13093554HCID 13093554, compound

Product 1

HCID 13093548HCID 13093548, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

5-(2Naphthyl)oxazolidin-4-one-2-thione (2.0 g., 8.2 mmoles) was partially dissolved in 25 ml. of aqueous ethanol at 50° C. Hydrogen peroxide (30%, 7 ml. was added) and the mixture refluxed for 4 hours. The reaction mixture was cooled, diluted with chloroform and water and the organic layer separated. The organic layer was extracted with saturated sodium bicarbonate. The bicarbonate layer was carefully acidified with dilute hydrochloric acid and the precipitated product recovered by filtration. Recrystallization from toluene gave purified 5-(2-naphthyl)oxazolidine-2,4-dione [0.2 g., m.p. 187°-188° C., pnmr/CDCl3 /delta: 6.54 (s, 1H), 7.3-8.1 (m, 7H)].

Workup

  1. customat 50° C
  2. temperatureThe reaction mixture was cooled
  3. customthe organic layer separated
  4. extractionThe organic layer was extracted with saturated sodium bicarbonate
  5. filtrationthe precipitated product recovered by filtration
  6. customRecrystallization from toluene
  7. customgave
  8. custompurified 5-(2-naphthyl)oxazolidine-2,4-dione [0.2 g., m.p. 187°-188° C., pnmr/CDCl3 /delta: 6.54 (s, 1H), 7.3-8.1 (m, 7H)]

Sources & evidence

ORD record
ord-7ce50052fa5e4ca0830a778b2c8385fc
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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