反応 #46696

反応方程式

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

溶媒

water

acetic acid

反応条件

後処理

1. 1
   workup.STIRRINGwas stirred at 60° C. for 4 h
2. 2
   温度to cool
3. 3
   その他partitioned between ethyl acetate (150 ml) and 10% aqueous sodium metabisulfite (100 ml)
4. 4
   その他The organic layer was separated
5. 5
   乾燥dried over sodium sulphate
6. 6
   その他evaporated in vacuo

実験手順

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).

出典