Sodium Sulfite → HCID 9990528, compound

HRID 648995Notes

Reaction equation

HRID 648995 reaction equation
[CH2:1]([C:3]1[C:4](=[O:23])[N:5](C2C=CC(OC)=CC=2)[CH2:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:2].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O.C(#N)C>[CH2:1]([C:3]1[C:4](=[O:23])[NH:5][CH2:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 10358098HCID 10358098, compound

Product 1

HCID 9990528HCID 9990528, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ceric ammonium nitrate (542 g, 0.99 mol) in water (1L) is added dropwise over 45 minutes to a suspension of 3-ethyl-4-(4-fluorophenyl)-1,5-dihydro-1-(4-methoxyphenyl)-2H-pyrrol-2-one (103 g, 0.33 mol) in acetonitrile (2 L), while the temperature of the reaction mixture is maintained at 0°-10° C. After stirring 30 minutes sodium sulfite (125 g) is added. The mixture is stirred 30 minutes more and sodium bicarbonate (83 g) is added. After stirring an additional 30 minutes the mixture is concentrated to 1L and extracted with methylene chloride and ethyl acetate. The extracts are dried with magnesium sulfate, evaporated, and recrystallized from ethanol. Chromatography of this material on silica gel followed by drying under vacuum at 60° C. for 18 hr affords the title compound.

Workup

  1. temperatureis maintained at 0°-10° C
  2. additionis added
  3. stirringAfter stirring an additional 30 minutes the mixture
  4. concentrationis concentrated to 1L
  5. extractionextracted with methylene chloride and ethyl acetate
  6. dry with materialThe extracts are dried with magnesium sulfate
  7. customevaporated
  8. customrecrystallized from ethanol
  9. customby drying under vacuum at 60° C. for 18 hr

Sources & evidence

ORD record
ord-40b43f00825b43d48be958ef65a43b5e
Source dataset
uspto-grants-1988_04
Patent number
US04737511

Reaction notes

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