N-Iodosuccinimide → HCID 86704015, compound

HRID 1773926Notes

Reaction equation

HRID 1773926 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[I:12][C:11]1[NH:10][CH:9]=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178418822HCID 178418822, compound

Product 1

HCID 86704015HCID 86704015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenyl-1H-imidazole (4.75 g, 33 mmoles) in CH2Cl2 (250 mL) is added N-iodosuccinimide (6.75 g, 30 mmoles). After 2 hours at room temperature, CH2Cl2 is removed under reduced pressure. The residual solid is triturated in hot ACN (150 mL), cooled down to room temperature and filtered. The white-off solid is triturated in hot ACN (60 mL), cooled down to room temperature and stirred overnight at room temperature. After a filtration, 5-iodo-4-phenyl-1H-imidazole is obtained.

Workup

  1. customCH2Cl2 is removed under reduced pressure
  2. customThe residual solid is triturated in hot ACN (150 mL)
  3. filtrationfiltered
  4. customThe white-off solid is triturated in hot ACN (60 mL)
  5. temperaturecooled down to room temperature
  6. filtrationAfter a filtration

Sources & evidence

ORD record
ord-9bdb0bc373de4cf6a7e5f7c9a98582fb
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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