Potassium nitrosodisulfonate → HCID 22506843, compound

HRID 985571Notes

Reaction equation

HRID 985571 reaction equation
N(S([O-])(=O)=O)(S([O-])(=O)=[O:4])[O].[K+].[K+].[CH3:13][C:14]1([CH3:25])[CH2:22][C:21]2[C:16](=[C:17]([CH3:24])[CH:18]=[CH:19][C:20]=2[CH3:23])[NH:15]1>P([O-])([O-])([O-])=O.CO>[CH3:13][C:14]1([CH3:25])[CH2:22][C:21]2[C:16]([C:17]([CH3:24])=[CH:18][C:19](=[O:4])[C:20]=2[CH3:23])=[N:15]1

Participants

5

Reactant 2

HCID 3032624Potassium nitrosodisulfonateHCID 22506883HCID 22506883, compound

Product 1

HCID 22506843HCID 22506843, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1061PhosphateSolvent

Procedure

To a solution of 65% potassium nitrosodisulfonate (10.4 g, 25.2 mmol) in pH 6.86 phosphate buffer (320 ml) was added a solution of 2,3-dihydro-2,2,4,7-tetramethyl-1H-indole (2.21 g, 12.6 mmol) in methanol (50 ml) and stirred at room temperature for 1.5 hours. The reaction mixture was extracted three times with toluene. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to a column chromatography on a silica gel (hexane:ethyl acetate=5:1) and recrystallized from ethyl acetate-hexane to obtain 1.71 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted three times with toluene
  2. washwashed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-966f2ea89d5f40ecbcad78287c321149
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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