Dichloromethane → 1-(4-Methoxyphenyl)azetidine-2,3-dione

HRID 964727Notes

Reaction equation

HRID 964727 reaction equation
C(Cl)Cl.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:15][C:14](=C)[C:13]2=[O:17])=[CH:8][CH:7]=1.[O:18]=[O+][O-]>C(O)(C)C>[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:15][C:14](=[O:18])[C:13]2=[O:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24823OzoneHCID 108214802-Azetidinone, 1-(4-methoxyphenyl)-3-methylene-

Product 1

HCID 154214471-(4-Methoxyphenyl)azetidine-2,3-dione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 100 ml quantity of methylene chloride and 7.5 ml of isopropyl alcohol were added to 20 g of 1-(4-methoxyphenyl)3-methylene azetidine-2-one 9 and dissolved with stirring. The reaction mixture was cooled to -15° C. after which an ozone gas was introduced over a period of 30 minutes. The excess ozone gas was removed using nitrogen gas and 3 ml of thiodiethanol and 6 g of thiodicresol were added, while being warmed to room temperature and then stirred for 1 hour. The reaction mixture was filtered to remove the precipitated thiodiethanolsulfoxide and washed once with 5% aqueous sodium bicarbonate and twice with 50 ml of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure, giving 14 g of the title compound 10. The 1H-NMR spectrum of the compound was the same as that of an authentic sample. ##STR5##

Workup

  1. dissolutiondissolved
  2. additionwas introduced over a period of 30 minutes
  3. customThe excess ozone gas was removed
  4. additionwere added
  5. stirringstirred for 1 hour
  6. filtrationThe reaction mixture was filtered
  7. customto remove the precipitated thiodiethanolsulfoxide
  8. washwashed once with 5% aqueous sodium bicarbonate and twice with 50 ml of water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a202022982749a8b8fd3a7aa33219a1
Source dataset
uspto-grants-1998_06
Patent number
US05770729

Reaction notes

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