Chloroacetone → HCID 13200304, compound

HRID 1903230Notes

Reaction equation

HRID 1903230 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[S:18])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:24][C:25](=[O:27])[CH3:26]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([S:18][CH2:24][C:25](=[O:27])[CH3:26])=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 13200303HCID 13200303, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13200304HCID 13200304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(p-Fluorophenyl)quinolin-2-thione (5.05 g.) was added in portions to a stirred suspension of sodium hydride (1.0 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (30 ml.) at 0°-5°. When all the hydrogen had evolved, chloroacetone (1.83 g.) was added and the mixture was stirred at ambient temperature for 18 hr. The mixture was poured into ice-water (300 ml.) and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed with brine (75 ml.) and then dried (MgSO4). The solvent was evaporated and the residue was chromatographed on basic alumina (200 g., Brockmann Grade III), eluted with increasing concentrations of ethyl acetate in petroleum ether. The eluate obtained with 10% v/v ethyl acetate in petroleum ether was evaporated to give 3-(p-fluorophenyl)-2-(2-oxopropylthio)quinoline, m.p. 95°-96°.

Workup

  1. customat 0°-5°
  2. extractionextracted with ethyl acetate (3×100 ml.)
  3. extractionThe ethyl acetate extract
  4. washwas washed with brine (75 ml.)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on basic alumina (200 g., Brockmann Grade III)
  8. washeluted
  9. temperaturewith increasing concentrations of ethyl acetate in petroleum ether
  10. customThe eluate obtained with 10% v/v ethyl acetate in petroleum ether
  11. customwas evaporated

Sources & evidence

ORD record
ord-db94811dbfe248f99dd8df474cea72e2
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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