Methyl iodide → HCID 14416588, compound

HRID 1728950Notes

Reaction equation

HRID 1728950 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[NH:6][C:7]([C:12]#[N:13])=[C:8]([C:10]#[N:11])[N:9]=1.[H][H].I[CH3:17]>CN(C)C=O>[CH3:17][N:9]1[C:8]([C:10]#[N:11])=[C:7]([C:12]#[N:13])[N:6]=[C:5]1[O:4][CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14416606HCID 14416606, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14416588HCID 14416588, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride g; 60% in an oil dispersion) was added in small portions to a stirred solution of the above-identified 2-methoxy-4,5-imidazoledicarbonitrile (3.25 g; 0.022 mol) in dimethylformamide (25 mL). Hydrogen gas was evolved. The mixture was cooled, iodomethane (3.2 g) was slowly added and the mixture was stirred overnight. The mixture was poured into ice-water and extracted with chloroform. The combined chloroform extract was washed with water, dried (magnesium sulfate) and concentrated to dryness in vacuo. The residue was chromatographed (silica gel eluted with dichloromethanehexanes) and the product was crystallized from dichloromethane-hexanes to give 1.6 g (45%) of 1-methyl-2-methoxy-4,5-imidazoledicarbonitrile (top 65°-66 ° C.).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with chloroform
  3. extractionThe combined chloroform extract
  4. washwas washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated to dryness in vacuo
  7. customThe residue was chromatographed
  8. wash(silica gel eluted with dichloromethanehexanes)
  9. customthe product was crystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-496657bc18c5438e8c64e35228c5787f
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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