Water → HCID 18973414, compound

HRID 2394402Notes

Reaction equation

HRID 2394402 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([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16]([N:20]=[C:21]=[O:22])[CH:15]=1.O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[C:14]1([CH3:23])[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([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])[CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69303m-Tolyl isocyanateHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 18973414HCID 18973414, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Indole-4-carbaldehyde (435 mg) was dissolved in 8 ml of dimethylformamide at room temperature under an argon gas atmosphere, then 126 mg of sodium hydride (content 60%) was added to the resulting solution and the mixture was stirred for 30 minutes, then 439 mg of m-tolylisocyanate was added thereto and the resulting mixture was stirred for one hour. The reaction solution was added to 50 ml of water followed by extraction with ethyl acetate (50 ml×2). The resulting organic phase was washed with water (50 ml×2), dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure to give a crude product. This was subjected to silica gel chromatography (eluent: hexane/ethyl acetate=4/1) to give 736 mg of 1-(m-tolylcarbamoyl)indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 88%.

Workup

  1. stirringthe resulting mixture was stirred for one hour
  2. extractionfollowed by extraction with ethyl acetate (50 ml×2)
  3. washThe resulting organic phase was washed with water (50 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customto give a crude product

Sources & evidence

ORD record
ord-213ca568b87b47429d95804972a29a4f
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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