Sodium hydride → HCID 18317347, compound

HRID 1700438Notes

Reaction equation

HRID 1700438 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:13]2[C:12](=[O:14])[CH2:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][C:8]=2[NH:7][CH:6]=1)[CH3:4].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>CN(C)C=O>[CH2:3]([C:5]1[C:13]2[C:12](=[O:14])[CH2:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][C:8]=2[N:7]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 18317732HCID 18317732, compound

Product 1

HCID 18317347HCID 18317347, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (0.13 g, washed with hexane thrice) in dimethylformamide (10 ml) was added 3-ethyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.64 g), and the mixture was stirred at room temperature for 30 minutes. To the mixture was added a solution of methanesulfonylchloride (0.34 g) in dimethylformamide (1 ml), and the mixture was stirred at the same temperature for 24 hours and then at 40° C. for 5 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. The residue was recrystallized from diisopropylether and hexane to give colorless crystals of 3-ethyl-1-methanesulfonyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.26 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 24 hours
  2. waitat 40° C. for 5 hours
  3. customUnder reduced pressure, the solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from diisopropylether and hexane

Sources & evidence

ORD record
ord-2efa757d02b1432a9a6d45f5e1cc01f7
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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