반응 #46696

반응 방정식

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

용매

water

acetic acid

반응 조건

후처리

1. 1
   workup.STIRRINGwas stirred at 60° C. for 4 h
2. 2
   온도to cool
3. 3
   기타partitioned between ethyl acetate (150 ml) and 10% aqueous sodium metabisulfite (100 ml)
4. 4
   기타The organic layer was separated
5. 5
   건조dried over sodium sulphate
6. 6
   기타evaporated in vacuo

실험 절차

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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