Реакция #46696

Уравнение реакции

iodine

sulfuric acid

Intermediate 1

N-(2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

periodic acid

→

title compound

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

Растворители

water

acetic acid

Условия реакции

Обработка

1. 1
   workup.STIRRINGwas stirred at 60° C. for 4 h
2. 2
   Температураto cool
3. 3
   Другоеpartitioned between ethyl acetate (150 ml) and 10% aqueous sodium metabisulfite (100 ml)
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried over sodium sulphate
6. 6
   Другоеevaporated in vacuo

Методика

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).

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