Iodine → N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

HRID 2100695Notes

Reaction equation

HRID 2100695 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12].S(=O)(=O)(O)O.[I:22](O)(=O)(=O)=O.II>C(O)(=O)C.O>[I:22][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH:2]([NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH2:3]2

Participants

7

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 46899808N-(2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

Product 1

HCID 46899809N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamideYield 483.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Intermediate 1 (1.75 g, 7.32 mmol) was dissolved in glacial acetic acid (30 ml) and then treated with concentrated sulfuric acid (0.8 ml) followed by water (2.8 ml) with stirring. This mixture was then treated with periodic acid (0.23 eq., 0.38 g, 1.67 mmol) then iodine (0.43 eq., 800 mg, 3.15 mmol), and the whole mix was stirred at 60° C. for 3-4 h. The reaction mixture was allowed to cool and then partitioned between ethyl acetate and 10% aqueous sodium metabisulfite. The organic layer was separated and dried over sodium sulphate and evaporated in vacuo to give the title compound as a yellow oil (2.95 g).

Workup

  1. stirringwas stirred at 60° C. for 3-4 h
  2. temperatureto cool
  3. custompartitioned between ethyl acetate and 10% aqueous sodium metabisulfite
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a0d98854a6b4a3dab1dbd92705fe28e
Source dataset
uspto-grants-2009_08
Patent number
US07572819B2

Reaction notes

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