Methyl iodide → HCID 20322453, compound

HRID 840008Notes

Reaction equation

HRID 840008 reaction equation
[CH2:1]([C:3]1([CH3:21])[N:15]([CH3:16])[C:14]([CH2:18][CH3:19])([CH3:17])[CH2:13][C:5]2([NH:9][C:8](=[O:10])[N:7]([CH3:11])[C:6]2=[O:12])[CH:4]1[CH3:20])[CH3:2].[H-].[Na+].CI.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:3]1([CH3:21])[N:15]([CH3:16])[C:14]([CH2:18][CH3:19])([CH3:17])[CH2:13][C:5]2([N:9]([CH3:26])[C:8](=[O:10])[N:7]([CH3:11])[C:6]2=[O:12])[CH:4]1[CH3:20])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 20322577HCID 20322577, compound

Product 1

HCID 20322453HCID 20322453, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.95 g of Compound 64, obtained as described in Example 5, in 10 ml of dimethylformamide was added 0.67 g of 52.9% sodium hydride; the mixture was stirred overnight at room temperature. 2.26 g of methyl iodide were then added and the mixture was heated at 100° C for 15 hours, with stirring. After cooling the mixture, 100 ml of ice-water and 20 ml of a 20% aqueous potassium carbonate solution were added in turn; the mixture was then extracted with ethyl acetate. The extract was washed with water and dried over potassium carbonate. After removing the solvent from the extract, the residue was purified by column chromatography on silica gel (eluent: chloroform containing 2.5% of methanol), giving 2.9 g of Compound 136 as a white powder melting at 77° - 88° C.

Workup

  1. temperaturethe mixture was heated at 100° C for 15 hours
  2. stirringwith stirring
  3. additionwere added in turn
  4. extractionthe mixture was then extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over potassium carbonate
  7. customAfter removing the solvent from the extract
  8. customthe residue was purified by column chromatography on silica gel (eluent: chloroform containing 2.5% of methanol)

Sources & evidence

ORD record
ord-ab5f3aacc51b4a358e96f77c41ffdcf6
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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