Methyl iodide → 2-[1-(Dimethylcarbamoyl)ethylthio]-3-phenylquinoline

HRID 1903218Notes

Reaction equation

HRID 1903218 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][N:22]([CH3:43])[C:23]([CH2:25][S:26][C:27]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:24].IC>CCCCCC.O1CCCC1.O.C(O)(=O)C>[CH3:21][N:22]([CH3:43])[C:23]([CH:25]([S:26][C:27]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)[CH3:1])=[O:24]

Participants

10

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 204682172-(Dimethylcarbamoylmethylthio)-3-phenylquinolineHCID 178418339Butyllithium

Product 1

HCID 132002102-[1-(Dimethylcarbamoyl)ethylthio]-3-phenylquinoline

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of lithium di-isopropylamide [prepared from di-isopropylamine (6.2 ml.) and n-butyllithium (24.7 ml. of a 1.7 M solution in hexane) in dry tetrahydrofuran (100 ml.) at -78°. under argon] was added a solution of 2-(dimethylcarbamoylmethylthio)-3-phenylquinoline (6.6 g.) in dry tetrahydrofuran (50 ml.) at -60°. The mixture was then stirred for 15 min. at -60°. Iodomethane (2.7 ml.) was added and the mixture was allowed to warm up to ambient temperature. Glacial acetic acid (2.6 ml.) was then added, followed by water (200 ml.). The tetrahydrofuran phase was separated and retained, and the aqueous layer was extracted with ethyl acetate (2×30 ml.). The ethyl acetate and tetrahydrofuran phases were combined and dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (100 g. of Brockmann grade III) eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether on evaporation gave 2-[1-(dimethylcarbamoyl)ethylthio]-3-phenylquinoline as a viscous oil, which was used without further purification.

Workup

  1. customat -78°
  2. customThe tetrahydrofuran phase was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×30 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residual oil was chromatographed on basic alumina (100 g. of Brockmann grade III)
  7. washeluted
  8. temperaturewith increasing concentrations of chloroform in petroleum ether
  9. customThe eluate obtained with 20% v/v chloroform in petroleum ether on evaporation

Sources & evidence

ORD record
ord-34d005306b4a4c3a809703d81834c081
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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