Methyl iodide → HCID 13309879, compound

HRID 325445Notes

Reaction equation

HRID 325445 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11](=[O:19])[C:10]=12)=[O:5])[CH3:2].[CH3:20]I>CN(C=O)C.[Ag]=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH3:20])[C:11](=[O:19])[C:10]=12)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 13309870HCID 13309870, compound

Product 1

HCID 13309879HCID 13309879, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester (12.4 g) and methyl iodide (98 g) in DMF (1 liter) was added silver oxide (65 g) with stirring. The reaction mixture was stirred at room temperature for 18 hours. After removal of insoluble material the solution was evaporated under oil pump vacuum to dryness. The residue was extracted with chloroform several times. The combined chloroform extracts were washed with water, dried by magnesium sulfate, then evaporated under water aspirator vacuum to give the product as a white solid (8.2 g, 63% yield). Recrystallized from acetonitrile, m.p. 233°-236° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. customAfter removal of insoluble material the solution
  3. customwas evaporated under oil pump vacuum to dryness
  4. extractionThe residue was extracted with chloroform several times
  5. washThe combined chloroform extracts were washed with water
  6. dry with materialdried by magnesium sulfate
  7. customevaporated under water

Sources & evidence

ORD record
ord-daa0cadaf2cd4df49d141ab2d8a4557d
Source dataset
uspto-grants-1984_04
Patent number
US04440929

Reaction notes

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