N-Iodosuccinimide → 5-Iodo-2-methyl-1H-imidazole-4-carbonitrile

HRID 1487865Notes

Reaction equation

HRID 1487865 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]#[N:8])[N:6]=1.[I:9]N1C(=O)CCC1=O>C(#N)C>[I:9][C:4]1[NH:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178432957HCID 178432957, compound2×

Product 1

HCID 900304155-Iodo-2-methyl-1H-imidazole-4-carbonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 25-mL round-bottom flask, was placed a mixture of 2-methyl-1H-imidazole-4-carbonitrile (compound 16.3, 50 mg, 0.47 mmol), N-iodosuccinimide (116 mg, 0.52 mmol) in ACN (5 mL). The resulting solution was heated at reflux overnight, then cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1/2) to yield 60 mg (55%) of the title compound as a light yellow solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux overnight
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1/2)

Sources & evidence

ORD record
ord-c2e7f8662d6145b2861a6a00ddf5e93d
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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