p-Toluenesulfonic acid → HCID 53769491, compound

HRID 1417457Notes

Reaction equation

HRID 1417457 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[CH3:12][S:13][CH:14]([S:28]([CH3:30])=O)[C:15](=O)[CH:16]=[CH:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C1C=CC=CC=1>[CH3:12][S:13][C:14]1([S:28][CH3:30])[C:19]2[NH:20][C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18]=2[CH2:17][C:16](=[O:8])[CH2:15]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 53652301HCID 53652301, compound

Product 1

HCID 53769491HCID 53769491, compoundYield 885.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

680 mg of p-toluenesulfonic acid was added to a mixture of 10.6 g of 3-(4-methylthio-4-methylsulfinyl-3-oxobutene-1-yl)indole, as obtained in Example 1(b), in 150 ml of tetrahydrofuran and 40 ml of benzene. The reaction mixture was next refluxed for 3 hours and then neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The solvent was removed from the resulting mixture by evaporation under reduced pressure and ethyl acetate was added to the residue. The aqueous layer was then extracted with ethyl acetate, and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 300 g of silica gel with a 9:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 9.7 g of the title compound as an amorphous solid.

Workup

  1. temperatureThe reaction mixture was next refluxed for 3 hours
  2. customThe solvent was removed from the resulting mixture by evaporation under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. extractionThe aqueous layer was then extracted with ethyl acetate
  5. extractionthe organic extract
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. additionwith a 9:1 v/v mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1e01da29cb99434faeaedda32a6203cb
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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