Cyclohexanone → HCID 23152581, compound

HRID 1012305Notes

Reaction equation

HRID 1012305 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C[O-].[Na+]>CO>[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=3)=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 10942334Sodium MethoxideHCID 23152479HCID 23152479, compound

Product 1

HCID 23152581HCID 23152581, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-tert-butyl-1H-indole-6-sulfonamide (3.60 g, 14.2 mmol) and cyclohexanone (4.50 ml, 43.4 mmol) in methanol (72 ml) was added 28% sodium methoxide in methanol solution (17 ml), and the mixture was stirred for 12 hr with heating under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. 2N Hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1) to give N-tert-butyl-3-(cyclohex-1-enyl)-1H-indole-6-sulfonamide (2.82 g, yield 59.7%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. addition2N Hydrochloric acid was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1)

Sources & evidence

ORD record
ord-8067c83f2ca4468d8a9dc646cbfdd14a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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