Potassium Hydroxide → HCID 18462070, compound

HRID 2303962Notes

Reaction equation

HRID 2303962 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]=[O:15].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])[CH:9]=[C:8]2[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 827585-Methoxyindole-3-carbaldehydeHCID 960701-Bromo-5-chloropentane

Product 1

HCID 18462070HCID 18462070, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of powdered potassium hydroxide in methyl sulfoxide is added dropwise a solution of 5-methoxyindole-3-carboxaldehyde in methyl sulfoxide. The mixture is stirred for 30 min and 1-bromo-5-chloropentane is added dropwise. The mixture is stirred for 1 h and partitioned between ethyl acetate and water. The combined organic extracts are washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product.

Workup

  1. stirringThe mixture is stirred for 1 h
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic extracts are washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give the product

Sources & evidence

ORD record
ord-cd7aa6557dab4929bff57737571e9eb2
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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