Sodium hydride → 2-((2-(Dimethylamino)-2-methylpropyl)thio)-3-phenylquinoline hydrochloride

HRID 1903238Notes

Reaction equation

HRID 1903238 reaction equation
[C:1]1([C:7]2[C:8](=[S:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Cl.[Cl:23][CH2:24][C:25]([N:28]([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C)C=O>[ClH:23].[CH3:29][N:28]([CH3:30])[C:25]([CH3:27])([CH3:26])[CH2:24][S:17][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 132002063-Phenylquinolin-2-thioneHCID 227322711-Chloro-2-dimethylamino-2-methylpropane hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 98858482-((2-(Dimethylamino)-2-methylpropyl)thio)-3-phenylquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Phenylquinolin-2-thione (1.4 g.) was added to a suspension of sodium hydride (0.68 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (10 ml.) at 0°-5°. When all the hydrogen had evolved, a slurry of 1-chloro-2-dimethylamino-2-methylpropane hydrochloride (1.1 g.) in dimethylformamide (10 ml.) was added and the mixture was stirred at ambient temperature for 20 hr. The mixture was then poured into ice-water (100 ml.) and extracted with ethyl acetate (3×30 ml.). The ethyl acetate extract was washed with brine (30 ml.) and then dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (125 g., Brockmann Grade III), eluted with increasing concentrations of methylene dichloride in petroleum ether. The eluate obtained with 10% v/v methylene dichloride in petroleum ether was evaporated, the residual oil was dissolved in diethyl ether (20 ml.), and ethereal hydrogen chloride was added until precipitation was complete. The mixture was filtered and the solid residue was crystallised from ethyl acetate to give 2-(2-dimethylamino-2-methylpropylthio)-3-phenylquinoline hydrochloride, m.p. 199°-201°.

Workup

  1. customat 0°-5°
  2. extractionextracted with ethyl acetate (3×30 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine (30 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residual oil was chromatographed on basic alumina (125 g., Brockmann Grade III)
  8. washeluted
  9. temperaturewith increasing concentrations of methylene dichloride in petroleum ether
  10. customThe eluate obtained with 10% v/v methylene dichloride in petroleum ether
  11. customwas evaporated
  12. dissolutionthe residual oil was dissolved in diethyl ether (20 ml.)
  13. additionethereal hydrogen chloride was added until precipitation
  14. filtrationThe mixture was filtered
  15. customthe solid residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-9d6cef58928841afb6486511a00970c1
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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