Sodium hydride → HCID 18317796, compound

HRID 1700443Notes

Reaction equation

HRID 1700443 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:18][C:17]2[NH:16][CH:15]=[C:14]([CH3:19])[C:13]=2[C:12](=[O:20])[CH2:11]1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:18][C:17]2[N:16]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:15]=[C:14]([CH3:19])[C:13]=2[C:12](=[O:20])[CH2:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 18317657HCID 18317657, compound

Product 1

HCID 18317796HCID 18317796, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.18 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 6-(2-chlorophenyl)-3-methyl-4,5,6,7-tetrahydroindol-4-one (1.0 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added methanesulfonylchloride (0.53 g) in dimethylformamide (3 ml), and the mixture was stirred at the same temperature for 9 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The mixture was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane), and the resulting crystals were recrystallized from ethyl acetate-hexane to give colorless crystals of 6-(2-chlorophenyl)-1-methanesulfonyl-3-methyl-4,5,6,7-tetrahydroindol-4-one (0.3 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 9 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe mixture was washed with sodium hydrogen carbonate solution, 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)
  8. customthe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-86723ed8ffe348629e96880f0c0343f4
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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