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

HRID 18418

Reaktionsgleichung

Reaktionsgleichung von HRID 18418
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 46899809N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamideAusbeute 437,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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 (0.38 g, 1.67 mmol) then iodine (800 mg, 3.15 mmol), and the whole mix was stirred at 60° C. for 4 h. The reaction mixture was allowed to cool and then partitioned between ethyl acetate (150 ml) and 10% aqueous sodium metabisulfite (100 ml). The organic layer was separated and dried over sodium sulphate and evaporated in vacuo to give the title compound as a yellow oil (2.67 g, 100%); mass spectrum: Found 364 (MH−), C12H16INO2S requires 365; 1H-NMR (400 MHz, CDCl3) δ 1.39 (6H, m), 3.39 (2H, m), 3.18 (1H, m), 3.28 (2H, m), 4.38 (1H, m), 4.63 (1H, m), 6.97 (1H, d, J=8 Hz), 7.51 (1H, m), 7.56 (1H, m).

Aufarbeitung

  1. stirringwas stirred at 60° C. for 4 h
  2. temperatureto cool
  3. custompartitioned between ethyl acetate (150 ml) and 10% aqueous sodium metabisulfite (100 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62a439a914c246d696dd6587eb6c8a22
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741351B2

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