تفاعل #64646

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred at room temperature for 16 h
2. 2
   تركيزThe mixture was concentrated in vacuo
3. 3
   أخرىthe residue was partitioned between 150 ml CH2Cl2 and 100 ml water
4. 4
   غسيلThe organic layer was washed with water and brine
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   workup.ADDITIONtreated with 20 ml 1N HCl/ether
8. 8
   أخرىevaporated to dryness
9. 9
   أخرىThe residue was triturated with 100 ml hot EtOAc
10. 10
    ترشيحfiltered
11. 11
    أخرىto collect the solid
12. 12
    أخرىThe solid was dried in vacuo
13. 13
    أخرىto give the product in 81% (5.3 g)
14. 14
    أخرىyield

الإجراء التجريبي

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.

المصدر