Water → HCID 21481001, compound

HRID 1490327Notes

Reaction equation

HRID 1490327 reaction equation
[H-].[K+].[C:3]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([O:28][CH3:29])=[C:23]([O:30][CH3:31])[CH:22]=2)(=[O:5])[CH3:4].[CH3:32]OS(OC)(=O)=O.O>CS(C)=O>[C:3]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:10]=1[C:19]1[N:20]([CH3:32])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([O:28][CH3:29])=[C:23]([O:30][CH3:31])[CH:22]=2)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 82127Potassium hydrideHCID 21481008HCID 21481008, compound

Product 1

HCID 21481001HCID 21481001, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In dimethyl sulfoxide was slowly suspended 480 mg of 35% potassium hydride, and 1.37 g of 2-[2-(2-acetamidoethyl)-4,5-dimethoxyphenyl]-5,6-dimethoxyindole was added to the suspension, followed by stirring for 10 minutes. To the mixture was further added 700 mg of dimethylsulfate, followed by stirring for 30 minutes. The reaction mixture was poured into water and extracted with methylene chloride. The extract was washed successively with water and a saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. Recrystallization of the residue from ethanol yielded 1.20 g of the title compound.

Workup

  1. additionwas added to the suspension
  2. stirringby stirring for 30 minutes
  3. extractionextracted with methylene chloride
  4. washThe extract was washed successively with water
  5. customa saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure
  6. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-a80a226c14ef45a39d26cc8a51c9edfc
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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