Sodium hydride → 1H-Indole-3-sulfonic Acid Dimethylamide

HRID 23397Notes

Reaction equation

HRID 23397 reaction equation
CN([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])C.[H-].[Na+]>CN(C=O)C>[CH3:17][N:16]([CH3:18])[S:13]([C:12]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][CH:4]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22574107C-[2-(dimethylamino-methyleneamino)-phenyl]-N,N-dimethyl-methanesulfonamide

Product 1

HCID 695460711H-Indole-3-sulfonic Acid DimethylamideYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

The crude product from Step 3 was dissolved in DMF (7 ml) and to this solution was added sodium hydride (60% in oil, 0.353 g, 8.82 mmole) in portions under a nitrogen atmosphere. After the initial bubbling subsided, the temperature was raised to 40° C. and left at that temperature overnight. Tlc analysis of the reaction mixture showed the presence of starting material and thus the temperature was raised to 60° C. and heated another 24 h. After cooling the reaction mixture was partitioned between 1.5 M HCl and ethyl acetate. The organic layer was separated and washed with bicarbonate solution, and then with brine. After drying over magnesium sulfate and filtration, the solvent was removed under reduced pressure to afford 0.547 g of the crude product. Purification by column chromatography (silica gel, 5:95 ethyl acetate:methylene chloride) afforded 0.437 g of the pure 1H-Indole-3-sulfonic acid dimethylamide (66% yield).

Workup

  1. customAfter the initial bubbling
  2. temperaturethus the temperature was raised to 60° C.
  3. temperatureheated another 24 h
  4. temperatureAfter cooling the reaction mixture
  5. customwas partitioned between 1.5 M HCl and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with bicarbonate solution
  8. dry with materialAfter drying over magnesium sulfate and filtration
  9. customthe solvent was removed under reduced pressure
  10. customto afford 0.547 g of the crude product
  11. customPurification by column chromatography (silica gel, 5:95 ethyl acetate:methylene chloride)

Sources & evidence

ORD record
ord-859a7472f97a4bb0beef2e3b7dfa771a
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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