Methyl iodide → HCID 20529171, compound

HRID 66821

Reaction equation

HRID 66821 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:28])[C:13]([CH3:18])=[C:12]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 205292015-Benzyloxy-3-(3-chloro-phenyl)-2-methyl-1H-indole

Product 1

HCID 20529171HCID 20529171, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 3.21 g (9.25 m mole) of 5-benzyloxy-3-(3-chloro-phenyl)-2-methyl-1H-indole was dissolved in 50 ml of absolute dimethylformamide, and the solution was mixed with 406 mg (9.3 m mole) of 55% sodium hydride in paraffin oil. After one hour 1.45 g (10.2 m mole) of methyliodide were added, and the mixture was stirred overnight. After evaporation, the reaction mixture was mixed with water and extracted with chloroform. The extracts, which were dried over sodium sulfate, were evaporated, and the residue obtained was purified by chromatography on silicagel by using toluene as solvent.

Workup

  1. customAfter evaporation
  2. additionthe reaction mixture was mixed with water
  3. extractionextracted with chloroform
  4. dry with materialThe extracts, which were dried over sodium sulfate
  5. customwere evaporated
  6. customthe residue obtained
  7. customwas purified by chromatography on silicagel

Sources & evidence

ORD record
ord-9be5438826f3452d949f2a84691685a7
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Linked notes

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