Sodium hydride → HCID 18317470, compound

HRID 1700437Notes

Reaction equation

HRID 1700437 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:11](=[O:13])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:8][C:7]=2[NH:6][CH:5]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>CN(C)C=O>[CH3:20][S:21]([N:6]1[C:7]2[CH2:8][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][C:11](=[O:13])[C:12]=2[C:4]([CH3:3])=[CH:5]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 183173703-Methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one

Product 1

HCID 18317470HCID 18317470, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.085 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 3-methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.4 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added a solution of methanesulfonylchloride (0.22 g) in dimethylformamide (2 ml), and the mixture was stirred at the same temperature for 18 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 1-methanesulfonyl-3-methyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.50 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 18 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-3ebb3f257ad947819c856f41b8b73fde
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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