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

HRID 36368

Reaction equation

HRID 36368 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH2:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]1=[O:22].[H-].[Na+].[CH2:32]([SH:35])[CH2:33][CH3:34]>C1COCC1>[ClH:2].[C:16]1([N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][S:35][CH2:32][CH2:33][CH3:34])([CH2:23][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)[C:8]2=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 194389643-(4-Chlorobutyl)-1,3-dihydro-1-phenyl-(4-pyridinylmethyl)-2H-indol-2-one hydrochloride

Product 1

HCID 194389591,3-Dihydro-1-phenyl-3[4-(propylthio)butyl]-3-(4-pyridinylmethyl)-2H-indol-2-one Hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. stirringstirred at room temperature for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between 150 ml CH2Cl2 and 100 ml water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. additiontreated with 20 ml 1N HCl/ether
  8. customevaporated to dryness
  9. customThe residue was triturated with 100 ml hot EtOAc
  10. filtrationfiltered
  11. customto collect the solid
  12. customThe solid was dried in vacuo
  13. customto give the product in 81% (5.3 g)
  14. customyield

Sources & evidence

ORD record
ord-16c39c3ed5994a42a5d391ab6bc9e3e5
Source dataset
uspto-grants-1995_05
Patent number
US05414004

Linked notes

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