Water → N-(1-benzoyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamide

HRID 1359143Notes

Reaction equation

HRID 1359143 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Na+].[OH2:17]>ClCCl>[C:3]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)(=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 18182841N-(2,3-Dihydro-1H-indol-5-YL)methanesulfonamide

Product 1

HCID 9922932N-(1-benzoyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(2,3-dihydro-1H-indole-5-yl)-methanesulfonamide (20 mg, 0.095 mmol) was dissolved in anhydrous dichloromethane (3 ml), sodium hydride (0.010 g, 50% in oil) was added and then, benzolychloride (0.011 ml, 0.095 mmol) was added at a temperature under −20° C. The resulting solution was stirred at the same temperature for 1 hour, stirred again at room temperature for 24 hours to complete the reaction. After pouring water (3 ml), dichloromethane layer was separated, washed with brine, dried over anhydrous magnesium sulfate and then, concentrated under reduced pressure. Afterward, the residue was purified through flash column chromatography (an eluent: ethyl acetate/n-hexane=1/1, v/v) and triturated with isooctane. As a result, the present compound (15 mg, productive yield 50%) was obtained as a solid.

Workup

  1. additionbenzolychloride (0.011 ml, 0.095 mmol) was added at a temperature under −20° C
  2. stirringstirred again at room temperature for 24 hours
  3. customthe reaction
  4. customwas separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customAfterward, the residue was purified through flash column chromatography (an eluent
  9. customethyl acetate/n-hexane=1/1, v/v) and triturated with isooctane
  10. customAs a result, the present compound (15 mg, productive yield 50%) was obtained as a solid

Sources & evidence

ORD record
ord-ed162bd852f940d694f6215d2011d14c
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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