Methanol → HCID 59676095, compound

HRID 2040483Notes

Reaction equation

HRID 2040483 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3S[CH2:7][C:6]2=1.O[O:21][S:22]([O-:24])=O.[K+].[CH3:26]O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:26])[C:11]1[C:10]3[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=3[S:22](=[O:24])(=[O:21])[CH2:7][C:6]2=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2891388-Methoxy-6,11-dihydrothiochromeno[4,3-b]indoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 59676095HCID 59676095, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-methoxy-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (257 mg, 0.915 mmoL) in MeOH (3 mL) and water (3 mL) was treated with OXONE (2.744 mmoL, 1.68 g) at room temperature. The reaction mixture was stirred for 6 hours. The solvent was removed and the residue was partitioned between EtOAc and saturated NaHCO3. The aqueous phase was extracted two times with EtOAc. The organic layer from each extraction was combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown solid. The crude material (the oil) was then purified by column chromatography (silica gel, 1:1 hexanes:EtOAc as eluent) to yield the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and saturated NaHCO3
  3. extractionThe aqueous phase was extracted two times with EtOAc
  4. extractionThe organic layer from each extraction
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a brown solid
  10. customThe crude material (the oil) was then purified by column chromatography (silica gel, 1:1 hexanes:EtOAc as eluent)

Sources & evidence

ORD record
ord-7eb10423a1824bc48e5f019bf18e251d
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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