N-Iodosuccinimide → HCID 178432758, compound

HRID 1488012Notes

Reaction equation

HRID 1488012 reaction equation
[CH:1]([C:4]1[NH:5][CH:6]=[C:7]([CH3:9])[N:8]=1)([CH3:3])[CH3:2].[I:10]N1C(=O)CCC1=O>C(#N)C>[I:10][C:6]1[NH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:8][C:7]=1[CH3:9]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178430870HCID 178430870, compound

Product 1

HCID 178432758HCID 178432758, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Isopropyl-4-methyl-1H-imidazole (3.96 g, 32 mmol) and N-iodosuccinimide (8.33 g, 35 mmol) were dissolved in acetonitrile (100 mL) and heated to reflux for 16 hours. The reaction was concentrated under reduced pressure and the residue was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; 0-40% EtOAc in hexane) to give 4.87 g (61%) of the title compound as a yellow solid. m/z (ES+) 251 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customthe residue was partitioned between EtOAc (50 mL) and water (50 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (SiO2; 0-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-78ff9e7ede4d45bc97c2476f256cd6f9
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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