Sodium hydride → HCID 14001273, compound

HRID 364922Notes

Reaction equation

HRID 364922 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[S:15])[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22].[H][H].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][Cl:30]>CN(C)C=O.O>[ClH:30].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][S:15][C:7]1[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[C:5]([O:4][CH3:3])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 140012434-Methoxy-3-(2-methylphenyl)quinoline-2(1H)-thioneHCID 178418361HCID 178418361, compound

Product 1

HCID 14001273HCID 14001273, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.25 g. of a 50% w/w dispersion in mineral oil) was added to a solution of 4-methoxy-3-o-tolylquinolin-2-thione (0.7 g.) in dimethylformamide (10 ml.) at ambient temperature. When all the hydrogen had evolved, 2-dimethylaminoethyl chloride hydrochloride (0.36 g.) was added and the mixture was stirred at ambient temperature for 20 hr. The reaction mixture was then poured into water (100 ml.) and extracted with ethyl acetate (2×25 ml.). The ethyl acetate extract was washed with water (2×10 ml.) and then dried (MgSO4). The ethyl acetate was evaporated, the residue was dissolved in diethyl ether (50 ml.), and ethereal hydrogen chloride was added until precipitation was complete. The mixture was filtered and the solid residue was crystallised from ethanoldiethyl ether to give 2-(2-dimethylaminoethylthio)-4-methoxy-3-o-tolylquinoline hydrochloride, m.p. 196°-8°.

Workup

  1. extractionextracted with ethyl acetate (2×25 ml.)
  2. extractionThe ethyl acetate extract
  3. washwas washed with water (2×10 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe ethyl acetate was evaporated
  6. dissolutionthe residue was dissolved in diethyl ether (50 ml.)
  7. additionethereal hydrogen chloride was added until precipitation
  8. filtrationThe mixture was filtered
  9. customthe solid residue was crystallised from ethanoldiethyl ether

Sources & evidence

ORD record
ord-d1e34de4a1ec42bb957351d427bb43dc
Source dataset
uspto-grants-1986_08
Patent number
US04607039

Reaction notes

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