Sodium hydride → HCID 70485975, compound

HRID 1903224Notes

Reaction equation

HRID 1903224 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:10](=[S:19])[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl.[Cl:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[NH2:30]>CN(C)C=O.O>[ClH:23].[NH2:30][C@@H:25]1[CH2:26][CH2:27][CH2:28][CH2:29][C@H:24]1[S:19][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 132002063-Phenylquinolin-2-thioneHCID 67351815HCID 67351815, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70485975HCID 70485975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.68 g. of a 50% w/w dispersion in mineral oil) was added to a solution of 3-phenylquinolin-2-thione (1.6 g.) in dimethylformamide (10 ml.) at ambient temperature. When all the hydrogen had evolved, trans-2-chlorocyclohexylamine hydrochloride (1.2 g.) was added and the reaction mixture was stirred at 60° for 20 hr. The reaction mixture was cooled to ambient temperature, diluted with water (100 ml.), and extracted with ethyl acetate (2×30 ml.). The ethyl acetate extract was washed with water (2×10 ml.) and then dried (MgSO4). The solvent was evaporated and the residue was chromatographed on basic alumina (100 g., Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether, followed by chloroform. The chloroform eluate was evaporated. The residue was dissolved in diethyl ether (100 ml.), and ethereal hydrogen chloride was added until precipitation was complete. The solvent was evaporated and the residue was crystallised from ethyl acetate to give 2-(trans-2-aminocyclohexylthio)-3-phenylquinoline hydrochloride, m.p. 223°- 5°.

Workup

  1. extractionextracted with ethyl acetate (2×30 ml.)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (2×10 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on basic alumina (100 g., Brockmann Grade III)
  7. washeluted
  8. temperaturewith increasing concentrations of chloroform in petroleum ether
  9. customThe chloroform eluate was evaporated
  10. dissolutionThe residue was dissolved in diethyl ether (100 ml.)
  11. additionethereal hydrogen chloride was added until precipitation
  12. customThe solvent was evaporated
  13. customthe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-05a85727fdc241e19b7c2c2eec35c2df
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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