p-Chlorothiophenol → 8-(4-Chlorophenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride

HRID 231540Notes

Reaction equation

HRID 231540 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[H][H].Cl.Cl[CH:15]1[C:24]2[N:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:18][CH2:17][CH2:16]1>CN(C)C=O>[ClH:3].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 137121818-Chloro-5,6,7,8-tetrahydroquinoline hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 142812488-(4-Chlorophenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.65 g (55 mmol) of sodium hydride (80%) were added in portions to a stirred solution of 3.62 g (25 mmol) of 4-chloro-benzenethiol in 36 ml of dry dimethylformamide under nitrogen and cooled in ice. After evolution of hydrogen had ceased, 4.80 g (20 mmol) of 8-chloro-5,6,7,8-tetrahydroquinoline hydrochloride were added and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure in a stream of nitrogen below 50° C. and 4N aqueous sodium hydroxide was added. The mixture was extracted with ethyl acetate and the extracts were washed with ice-cold aqueous sodium hydroxide and then with aqueous saturated sodium chloride, dried over MgSO4 and evaporated to dryness under reduced pressure. A solution of the resulting oil in ether was treated with ethereal hydrogen chloride to precipitate 5.13 g (82%) of 8-(4-chlorophenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride as colorless crystals (from ethanol-ether).

Workup

  1. temperaturecooled in ice
  2. customThe solvent was removed under reduced pressure in a stream of nitrogen below 50° C. and 4N aqueous sodium hydroxide
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extracts were washed with ice-cold aqueous sodium hydroxide
  6. dry with materialwith aqueous saturated sodium chloride, dried over MgSO4
  7. customevaporated to dryness under reduced pressure
  8. additionA solution of the resulting oil in ether was treated with ethereal hydrogen chloride
  9. customto precipitate 5.13 g (82%) of 8-(4-chlorophenylthio)-5,6,7,8-tetrahydroquinoline hydrochloride as colorless crystals (from ethanol-ether)

Sources & evidence

ORD record
ord-647ec7380877452da48200e60fe8b801
Source dataset
uspto-grants-1989_07
Patent number
US04847268

Reaction notes

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