Sodium hydride → Ethanamine, N,N-dimethyl-2-((3-phenyl-2-quinolinyl)thio)-, hydrochloride (1:1)

HRID 1903215Notes

Reaction equation

HRID 1903215 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[H-].[Na+].[H][H].[Cl:12][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>CN(C)C=O>[ClH:12].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][S:6][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25798Captamine HydrochlorideHCID 42560782-Chloro-3-phenylquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 174433Ethanamine, N,N-dimethyl-2-((3-phenyl-2-quinolinyl)thio)-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Dimethylaminoethanethiol hydrochloride (58.40 g. of 80% w/w) was added to a suspension of sodium hydride (31.68 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (500 ml.) at 0° to 5°. When all the hydrogen had evolved, a solution of 2-chloro-3-phenylquinoline (72.70 g.) in dimethylformamide (100 ml.) was added and the mixture stirred and heated at 75° for 5 hr. The reaction mixture was then poured into ice water (4000 ml.) and extracted with ethyl acetate (6×500 ml.). The ethyl acetate extract was washed succesively with water (1000 ml.) and saturated brine (1000 ml.), and then dried (MgSO4). The ethyl acetate solution was evaporated and the residual oil was chromatographed on basic alumina (1200 g.; Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether. The elutate obtained with 10% v/v chloroform in petroleum ether was evaporated. The residual solid was dissolved in ethanol (800 ml.) and treated with concentrated hydrochloric acid (25.2 ml.). The ethanol was evaporated, and the oily residue was azeotroped with toluene. The solid obtained was recrystallised from ethanol-diethyl ether and was then washed with a small volume of cold acetone. The mixture was filtered and there was obtained as the solid residue 2-(2-dimethylaminoethylthio)-3-phenylquinoline hydrochloride, m.p. 195°-8° C.

Workup

  1. customat 0° to 5°
  2. temperatureheated at 75° for 5 hr
  3. extractionextracted with ethyl acetate (6×500 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed succesively with water (1000 ml.) and saturated brine (1000 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe ethyl acetate solution was evaporated
  8. customthe residual oil was chromatographed on basic alumina (1200 g.; Brockmann Grade III)
  9. washeluted
  10. temperaturewith increasing concentrations of chloroform in petroleum ether
  11. customThe elutate obtained with 10% v/v chloroform in petroleum ether
  12. customwas evaporated
  13. dissolutionThe residual solid was dissolved in ethanol (800 ml.)
  14. additiontreated with concentrated hydrochloric acid (25.2 ml.)
  15. customThe ethanol was evaporated
  16. customthe oily residue was azeotroped with toluene
  17. customThe solid obtained
  18. customwas recrystallised from ethanol-diethyl ether
  19. washwas then washed with a small volume of cold acetone
  20. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-8b9f4e933005473ea114d64ef89d4c72
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

Loading…