Реакция #64646

Уравнение реакции

3-(4-Chlorobutyl)-1,3-dihydro-1-phenyl-(4-pyridinylmethyl)-2H-indol-2-one hydrochloride

NaH

propanethiol

→

1,3-Dihydro-1-phenyl-3[4-(propylthio)butyl]-3-(4-pyridinylmethyl)-2H-indol-2-one Hydrochloride

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at room temperature for 16 h
2. 2
   КонцентрированиеThe mixture was concentrated in vacuo
3. 3
   Другоеthe residue was partitioned between 150 ml CH2Cl2 and 100 ml water
4. 4
   ПромывкаThe organic layer was washed with water and brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   workup.ADDITIONtreated with 20 ml 1N HCl/ether
8. 8
   Другоеevaporated to dryness
9. 9
   ДругоеThe residue was triturated with 100 ml hot EtOAc
10. 10
    Фильтрацияfiltered
11. 11
    Другоеto collect the solid
12. 12
    ДругоеThe solid was dried in vacuo
13. 13
    Другоеto give the product in 81% (5.3 g)
14. 14
    Другоеyield

Методика

3-(4-Chlorobutyl)-1,3-dihydro-1-phenyl-(4-pyridinylmethyl)-2H-indol-2-one hydrochloride (6.0 g, 14.04 mmol) in 75 ml dry THF was treated with NaH (0.75 g, 31.25 mmol) and stirred for 10 min. under dry nitrogen. The mixture was then treated with propanethiol (1.2 g, 15.4 mmol) and stirred at room temperature for 16 h. The mixture was concentrated in vacuo, and the residue was partitioned between 150 ml CH2Cl2 and 100 ml water. The organic layer was washed with water and brine, dried over MgSO4, filtered, treated with 20 ml 1N HCl/ether, and evaporated to dryness. The residue was triturated with 100 ml hot EtOAc, cooled to room temperature, and filtered to collect the solid. The solid was dried in vacuo to give the product in 81% (5.3 g) yield; mp 149°-150° C.; IR(KBr): C=O 1717 cm-1 ; NMR(DMSOd6TMS): δ0.90 (t, 3H, CH3), 1.02, 1.18 (2m, 2H, SCCCH2), 1.45 (m, 4H, CH2CSCCH2), 2.1 (SCCCCH2), 2.37 (2t, 4H, CH2SCH2), [3.42 (d, 1H), 3.59 (d, 1H), CH2 -Pyr], [6.53 (m, 1H), 7.19 (m, 2H), 7.44 (d, 3H), 7.53 (m, 2H), 7.65 (m, 1H) Ar], 7.10, 8.66 (2d, 4H, 4-Pyr]; mass spec m/e 431 (M+1)-HCl.

Источник