反应 #64646

反应方程式

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

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at room temperature for 16 h
2. 2
   浓缩The mixture was concentrated in vacuo
3. 3
   其他the residue was partitioned between 150 ml CH2Cl2 and 100 ml water
4. 4
   洗涤The organic layer was washed with water and brine
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   workup.ADDITIONtreated with 20 ml 1N HCl/ether
8. 8
   其他evaporated to dryness
9. 9
   其他The residue was triturated with 100 ml hot EtOAc
10. 10
    过滤filtered
11. 11
    其他to collect the solid
12. 12
    其他The solid was dried in vacuo
13. 13
    其他to give the product in 81% (5.3 g)
14. 14
    其他yield

实验过程

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.

来源