Methyl iodide → HCID 21689292, compound

HRID 2081593Notes

Reaction equation

HRID 2081593 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[N:3]1[CH2:10][CH2:11][S:12][C:13]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=1.[H-].[Na+].I[CH3:26]>CN(C)C=O>[CH3:26][N:17]1[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=[C:13]1[S:12][CH2:11][CH2:10][N:3]1[C:2]([CH3:22])([CH3:1])[CH2:7][CH2:6][CH2:5][C:4]1([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67747621HCID 67747621, compound

Product 1

HCID 21689292HCID 21689292, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 ml of N,N-dimethylformamide was dissolved 200 mg of the compound obtained in Example 9, and 30.4 mg of 60% sodium hydride was added to the solution, followed by stirring for about 1 hour. To the mixture was added 0.48 ml of iodomethane, and the mixture was allowed to react at room temperature for 2 hours. The reaction mixture was extracted with 300 ml of chloroform, and the chloroform layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The residue was freed of the solvent by distillation under reduced pressure, and the resulting viscous brown liquid was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 by volume) to obtain 202 mg (97%) of the titled compound as a pale yellow powder.

Workup

  1. additionwas added to the solution
  2. customto react at room temperature for 2 hours
  3. extractionThe reaction mixture was extracted with 300 ml of chloroform
  4. washthe chloroform layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe residue was freed of the solvent by distillation under reduced pressure
  7. customthe resulting viscous brown liquid was purified by silica gel column chromatography (chloroform:methanol=50:1 to 10:1 by volume)

Sources & evidence

ORD record
ord-8aecd00c529947d2999c4080b423d6cc
Source dataset
uspto-grants-1993_02
Patent number
US05185347

Reaction notes

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