Methyl iodide → HCID 23116231, compound

HRID 499886Notes

Reaction equation

HRID 499886 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([CH2:38][CH3:39])=[C:7]([CH2:27][C:28]([N:30]([CH2:35][CH2:36][OH:37])[CH2:31][CH2:32][O:33][CH3:34])=[O:29])[C:8]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:42]I.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:4][C:5]1[C:6]([CH2:38][CH3:39])=[C:7]([CH2:27][C:28]([N:30]([CH2:35][CH2:36][O:37][CH3:42])[CH2:31][CH2:32][O:33][CH3:34])=[O:29])[C:8]([C:15](=[O:26])[C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:20][CH:21]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23116349HCID 23116349, compound

Product 1

HCID 23116231HCID 23116231, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[3,5-Diallyloxy-2-ethyl-6-(4-methanesulfonyl-benzoyl)phenyl]-N-(2-hydroxyethyl)-N-(2-methoxyethyl)-acetamide (450 mg, 0.76 mmol) obtained in Example 96, Step 1 was dissolved in N,N-dimethylformamide (10 mL), and a 60% sodium hydride dispersion in mineral oil (50 mg, 1.3 mmol) was added thereto in an atmosphere of argon with stirring under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes, and methyl iodide (0.05 mL, 0.8 mmol) was added dropwise thereto, followed by further stirring for 12 hours. After the reaction mixture was ice-cooled, a saturated aqueous solution of ammonium chloride was added thereto to stop the reaction, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1) to obtain 2-[3,5-diallyloxy-2-ethyl-6-(4-methanesulfonylbenzoyl)-phenyl]-N,N-bis(2-methoxyethyl)acetamide (95 mg, 21%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. stirringby further stirring for 12 hours
  4. temperaturecooled
  5. customthe reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-fc8139e28fc84d508350d5afdb1eeefd
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

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