Sodium hydride → 2-(Dimethylcarbamoylmethylthio)-3-phenylquinoline

HRID 1903217Notes

Reaction equation

HRID 1903217 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[CH2:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25]>CN(C)C=O.O>[CH3:27][N:26]([CH3:28])[C:24]([CH2:23][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)=[O:25]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 132002063-Phenylquinolin-2-thioneHCID 178418361HCID 178418361, compound

Product 1

HCID 204682172-(Dimethylcarbamoylmethylthio)-3-phenylquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Phenylquinolin-2-thione (4.74 g.; see Example 6) was added in portions to a well-stirred suspension of sodium hydride (1.06 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (25 ml.) at 0°-5°. After all the hydrogen gas had evolved, 2-chloro-N,N-dimethylacetamide (2.19 g.) was added and the mixture was heated at 80°. for 2 hr. The reaction mixture was then poured into water (300 ml.) and extracted with ethyl acetate (4×50 ml.). The ethyl acetate extract was washed with water (50 ml.) and then dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (70 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 was evaporated. The residual solid was crystallised from ethyl acetate-petroleum ether to give 2-(dimethylcarbamoylmethylthio)-3-phenylquinoline, m.p. 86°-9°.

Workup

  1. customat 0°-5°
  2. temperaturethe mixture was heated at 80°
  3. extractionextracted with ethyl acetate (4×50 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed with water (50 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe residual oil was chromatographed on basic alumina (70 g. of 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. customThe residual solid was crystallised from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-be9c82a7cc4a4ca68c06435a86acfc76
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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