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

HRID 36368

反応式

HRID 36368 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

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.

後処理

  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

出典と根拠

ORDレコード
ord-16c39c3ed5994a42a5d391ab6bc9e3e5
出典データセット
uspto-grants-1995_05
特許番号
US05414004

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