Acetone → Famoxadone

HRID 1588869Notes

Reaction equation

HRID 1588869 reaction equation
[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[O:6][C:5](=S)[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].CC(C)=[O:31]>O>[CH3:1][C:2]1([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[O:6][C:5](=[O:31])[N:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15]

Participants

4

Reactant 2

HCID 180AcetoneHCID 14796539HCID 14796539, compound

Product 1

HCID 213032Famoxadone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-methyl-5-(4-phenoxyphenyl)-3-phenylamino-2-thioxooxazolidin-4-one (2 g, 0.0051 moles) in 50 mls of acetone (0.1M) was treated at room temperature with a solution of KHSO5OXONE®, 4.72 g, 0.0154 moles) in 20 mls of water. The white slurry was heated at 50° C. for two hours then cooled to room temperature and filtered. The residue was washed with fresh acetone and the filtrates were evaporated under reduced pressure until all the acetone distilled away. The residue was dissolved in methylene chloride and washed with water and brine. The organic layer was dried (MgSO4), filtered, and evaporated to give the crude product. Recrystallization from 1-chlorobutane and petroleum ether afforded 1.68 g (88% of theoretical) of pure product as a white solid with a melting point of 140°-142° C.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered
  3. washThe residue was washed with fresh acetone
  4. customthe filtrates were evaporated under reduced pressure until all the acetone
  5. distillationdistilled away
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed with water and brine
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give the crude product
  12. customRecrystallization from 1-chlorobutane and petroleum ether
  13. customafforded 1.68 g (88% of theoretical) of pure product as a white solid with a melting point of 140°-142° C.

Sources & evidence

ORD record
ord-7bdccd13410c4ee482c293b483f06e3a
Source dataset
uspto-grants-1993_06
Patent number
US05223523

Reaction notes

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