Iodine chloride → HCID 18940886, compound

HRID 356037Notes

Reaction equation

HRID 356037 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[I:14]Cl>C(O)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([I:14])=[C:10]([Cl:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 45322241-Acetyl-6-chloroindoline

Product 1

HCID 18940886HCID 18940886, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Acetyl-6-chloroindoline (0.3 g, 1.53 mmol) and iodine monochloride (2.48 g, 15.3 mmol) in acetic acid (25 ml) were heated under reflux for 48 hours. After cooling the mixture was partitioned between ethyl acetate and 10% aqueous NaOH. The organic extract was washed with aqueous Na2 SO3 dried (Na2SO4) & evaporated to dryness under reduced pressure. Chromatography on silica gel using dichloromethane afforded the title compound (0.19 g, 39%).

Workup

  1. temperatureunder reflux for 48 hours
  2. temperatureAfter cooling the mixture
  3. customwas partitioned between ethyl acetate and 10% aqueous NaOH
  4. extractionThe organic extract
  5. washwas washed with aqueous Na2
  6. dry with materialSO3 dried (Na2SO4)
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0272105375aa4e03a8e08330b830de25
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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