4,4'-Dichlorodiphenyl sulfone → HCID 13505095, compound

HRID 746084Notes

Reaction equation

HRID 746084 reaction equation
[CH:1]1[C:6]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:5][CH:4]=[C:3](Cl)[CH:2]=1.[CH3:18][C:19]1[CH:20]=[C:21]([OH:26])[CH:22]=[CH:23][C:24]=1[NH2:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([C:6]2[CH:5]=[CH:4][C:3]([O:26][C:21]3[CH:22]=[CH:23][C:24]([NH2:25])=[C:19]([CH3:18])[CH:20]=3)=[CH:2][CH:1]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 66254,4'-Dichlorodiphenyl sulfoneHCID 11430Potassium CarbonateHCID 178194-Amino-m-cresol

Product 1

HCID 13505095HCID 13505095, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 250 mL flask equipped with stirrer, condenser, under nitrogen atmosphere, was added 20 g (0.070 mol) of 4,4'-dichlorodiphenylsulfone, 12.8 g (0.104 mol) of 3-methyl-4-aminophenol, 15.5 g (0.112 mol) of potassium carbonate, and 130 mL of dimethylformamide. The resulting mixture was stirred at room temperature for 24 hours and at 125° for 28 hours. It was cooled and concentrated. The concentrated material was dissolved in 400 mL of toluene and washed with 4% sodium hydroxide, followed by water and brine washes. The organic layer was dried over sodium sulfate, concentrated, and chromatographed through 350 g of florisil column. Elution with hexane/ethylacetate (8/2) afforded 11.2 g (0.030 mol) of a yellow solid; mp 200° D.

Workup

  1. customTo a 250 mL flask equipped with stirrer, condenser, under nitrogen atmosphere
  2. temperatureIt was cooled
  3. concentrationconcentrated
  4. dissolutionThe concentrated material was dissolved in 400 mL of toluene
  5. washwashed with 4% sodium hydroxide
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed through 350 g of florisil column
  9. washElution with hexane/ethylacetate (8/2)

Sources & evidence

ORD record
ord-ea9d714df47c4e0e89f193165621123d
Source dataset
uspto-grants-1986_07
Patent number
US04602109

Reaction notes

Loading…