Water → HCID 10107997, compound

HRID 1096486Notes

Reaction equation

HRID 1096486 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C.CCOC(C)=O>[C:14]1([S:20]([N:1]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=3[CH:3]=[CH:2]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 10107997HCID 10107997, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1H-Indole-4-carbaldehyde (24.8 g, 0.17 mol) was dissolved in dry DMF (500 ml), cooled in ice-bath and NaH (7.5 g (60% suspension in oil), 0.19 mol, 1.1 eq.) was added. After stirring for a few minutes, the cold bath was removed and the r×n mixture was stirred at room temperature for 40 min. under Ar. The insoluble NaH clumps were brought in solution by means of sonication for a few minutes. The mixture was cooled in ice-bath and benzenesulfonyl chloride (23.9 ml, 0.188 mol, 1.1 e.q.) was added dropwise over 3 min. The reaction mixture was stirred at room temperature for 1 hour, then poured slowly into a mixture of water (1 L) and EtOAc (200 ml). The aqueous phase was extracted with EtOAc (5×100 ml), the organic phase was washed with brine (200 ml), dried over Na2SO4 and evaporated. The residue was purified on silica flash column using petroleum ether/EtOAc (1:1) giving the product as a colorless crystalline solid. Yield: 45.5 g. MS m/z 286 [M+H]+.

Workup

  1. temperaturecooled in ice-bath
  2. customthe cold bath was removed
  3. stirringthe r×n mixture was stirred at room temperature for 40 min. under Ar
  4. customThe insoluble NaH clumps were brought in solution by means of sonication for a few minutes
  5. temperatureThe mixture was cooled in ice-bath
  6. stirringThe reaction mixture was stirred at room temperature for 1 hour
  7. extractionThe aqueous phase was extracted with EtOAc (5×100 ml)
  8. washthe organic phase was washed with brine (200 ml)
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customThe residue was purified on silica flash column

Sources & evidence

ORD record
ord-6b8ac0f6da8d46f79250e4ac216cffbd
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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