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

HRID 1435715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435715
[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 483,7 %

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 (0.23 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ac14732020c64a43b96a3461b9d59c79
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618969B2

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