Water → HCID 58955108, compound

HRID 1990983Notes

Reaction equation

HRID 1990983 reaction equation
[C:1]1([S:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:17][CH2:18][CH2:19][OH:20])[NH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[OH:22].[Na+].OOS([O-])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[OH2:40]>CC(C)=O.C(OCC)(=O)C>[C:1]1([S:7]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:17][CH2:18][CH2:19][OH:20])[NH:10][CH:9]=2)(=[O:22])=[O:40])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 58955097HCID 58955097, compound

Product 1

HCID 58955108HCID 58955108, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[3-(phenylthio)-1H-indol-4-yl]propan-1-ol (1.024 g, 3.61 mmol) in acetone (45 mL) was added a solution of sodium hydrogen carbonate (0.759 g, 9.03 mmol) in water (45 mL) followed by OXONE® (supplied by DuPont, potassium peroxymonosulfate as active ingredient) (5.55 g, 9.03 mol) and the reaction mixture stirred at room temperature for 26 hours. The acetone was removed in vacuo and the resulting suspension partitioned between ethyl acetate (120 mL) and water (100 mL). The organic phase was separated, washed with water (100 mL) and brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford a white foam. Ethyl acetate (30 mL) was added to the crude product and the mixture stirred vigorously for 2 hours then filtered to afford the title compound as a white solid (1.027 g, 90%). MS (ES−) m/z 314.0 (M−H).

Workup

  1. customThe acetone was removed in vacuo
  2. customthe resulting suspension partitioned between ethyl acetate (120 mL) and water (100 mL)
  3. customThe organic phase was separated
  4. washwashed with water (100 mL) and brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a white foam
  9. stirringthe mixture stirred vigorously for 2 hours
  10. filtrationthen filtered

Sources & evidence

ORD record
ord-ac8aa74d07a947e881f000dade03a8a9
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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