Methyl iodide → HCID 22627675, compound

HRID 278058Notes

Reaction equation

HRID 278058 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([NH:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH:11]([OH:15])[CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.I[CH3:22]>CN(C)C(=O)C.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:8][C:9](=[O:18])[C:10]([CH3:16])([CH3:17])[CH:11]([O:15][CH3:22])[CH:12]([CH3:13])[CH3:14])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22627676HCID 22627676, compound

Product 1

HCID 22627675HCID 22627675, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.25 g of a 60% dispersion in mineral oil, 5.1 mmol) in N,N-dimethylacetamide is added dropwise a solution of 4′-chloro-3-hydroxy-2,2,4-trimethylvaleranilide (1.5 g, 5.6 mmol) in N,N-dimethylacetamide. After stirring for 40 minutes at room temperature, iodomethane (1.58 g, 11.1 mmol) is added. The reaction mixture is stirred at room temperature for 18 hours, diluted with water, and extracted with ether. The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a semisolid. Flash column chromatography of the semi-solid using silica gel and an ethyl acetate/hexanes solution (1:10) gives the title product as a white solid (0.71 g, mp 103-107° C.) which is identified by 1H NMR spectral analysis.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 18 hours
  2. extractionextracted with ether
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a semisolid

Sources & evidence

ORD record
ord-0a96f4a19f6943a2a84d3ff7801798c2
Source dataset
uspto-grants-2002_03
Patent number
US06359009B1

Reaction notes

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