N-Iodosuccinimide → HCID 89656398, compound

HRID 930873Notes

Reaction equation

HRID 930873 reaction equation
[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[C:6]([Cl:8])[CH:7]=1.[I:11]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[C:6]([Cl:8])[C:7]=1[I:11]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 57662781HCID 57662781, compound

Product 1

HCID 89656398HCID 89656398, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of Example 74a (2.12 g, 13.3 mmol) and N-iodosuccinimide (5.38 g, 23.9 mmol) in acetonitrile (30 mL) was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20-40% ethyl acetate in hexanes to afford 3.27 g (86%) of the title compound.

Workup

  1. temperatureunder reflux for 6 hours
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting with 20-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5678692ba1e04e87bafa581491817e61
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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