Réaction #792231

Équation de réaction

5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one

1-(bromomethyl)-4-[(trifluoromethyl)sulphanyl]benzene

→

5-({4-[(Trifluoromethyl)sulphanyl]benzyl}oxy)-3,4-dihydroisoquinolin-1(2H)-one

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températureunder reflux for 6 h
2. 2
   TempératureAfter cooling
3. 3
   Filtrationthe insoluble constituents were filtered off
4. 4
   Autrethe solvent was removed under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   AutreThe phases were separated
7. 7
   Séchagethe organic phase was dried over sodium sulphate
8. 8
   Autrethe solvent was removed under reduced pressure
9. 9
   AutreThe crude product was purified by chromatography (ethyl acetate:n-heptane 2:1)

Mode opératoire

166 mg (1.017 mmol) of 5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one, 289 mg (1.068 mmol) of 1-(bromomethyl)-4-[(trifluoromethyl)sulphanyl]benzene and 365 mg (2.645 mmol) were suspended in 3 ml of ethanol and stirred under reflux for 6 h. After cooling, the insoluble constituents were filtered off and the solvent was removed under reduced pressure. The residue was dissolved in chloroform and water. The phases were separated, the organic phase was dried over sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified by chromatography (ethyl acetate:n-heptane 2:1). This gave 200 mg (54% of theory) of the desired 5-({4-[(trifluoromethyl)sulphanyl]benzyl}oxy)-3,4-dihydroisoquinolin-1(2H)-one. 1H-NMR (400 MHz, d6-DMSO δ, ppm) 7.89 (br. s, 1H), 7.52-7.44 (m, 4H), 7.28 (t, 1H), 7.22 (d, 1H), 5.16 (s, 2H), 3.33 (dt, 2H), 2.84 (t, 2H).

Source