Sodium hydride → HCID 3028230, compound

HRID 1903214Notes

Reaction equation

HRID 1903214 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]([CH:23]([CH3:25])[CH3:24])=[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]([CH:23]([CH3:25])[CH3:24])=[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 132002032-Chloro-3-(propan-2-yl)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 3028230HCID 3028230, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Dimethylaminoethanethiol hydrochloride (3.4 g.) was added to a suspension of sodium hydride (2.32 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (25 ml.) at 0° to 5°. When all the hydrogen had evolved, 2-chloro-3-isopropylquinoline (4.0 g.) was added and the mixture heated at 80° for 5 hr. The reaction mixture was then poured into ice water (500 ml.) and extracted with ethyl acetate (3×120 ml.). The ethyl acetate extract was washed successively with water (100 ml.) and saturated brine (100 ml.) and then dried (MgSO4). The ethyl acetate solution was evaporated and the residual oil was chromatographed on basic alumina (70 g.; Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether was evaporated, the residual oil was dissolved in diethyl ether, and ethereal hydrogen chloride was added until precipitation was complete. The solid residue was collected by filtration and crystallised from ethanol-diethyl ether to give 2-(2-dimethylaminoethylthio)-3-isopropylquinoline hydrochloride, m.p. 164°-7°.

Workup

  1. customat 0° to 5°
  2. temperaturethe mixture heated at 80° for 5 hr
  3. extractionextracted with ethyl acetate (3×120 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed successively with water (100 ml.) and saturated brine (100 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe ethyl acetate solution was evaporated
  8. customthe residual oil was chromatographed on basic alumina (70 g.; Brockmann Grade III)
  9. washeluted
  10. temperaturewith increasing concentrations of chloroform in petroleum ether
  11. customThe eluate obtained with 20% v/v chloroform in petroleum ether
  12. customwas evaporated
  13. dissolutionthe residual oil was dissolved in diethyl ether
  14. additionethereal hydrogen chloride was added until precipitation
  15. filtrationThe solid residue was collected by filtration
  16. customcrystallised from ethanol-diethyl ether

Sources & evidence

ORD record
ord-650981ac49164f219e7c2ccb18a693dc
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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