反応 #64646

反応方程式

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

溶媒

THF

反応条件

後処理

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

実験手順

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.

出典