Sodium hydride → HCID 20468237, compound

HRID 1903226Notes

Reaction equation

HRID 1903226 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[S:20])[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][CH:5]=1)([OH:3])=[O:2].[H-].[Na+].[H][H].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][Cl:30]>CN(C)C=O>[ClH:30].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([S:20][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 13200301HCID 13200301, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20468237HCID 20468237, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(p-Carboxyphenyl)quinolin-2-thione (6.87 g.) was added to a suspension of sodium hydride (3.9 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (50 ml.) at 0°-5°. When all the hydrogen had evolved, 2-dimethylaminoethyl chloride hydrochloride (3.5 g.) was added and the mixture was stirred at ambient temperature for 16 hr. The mixture was poured into ice-water (300 ml.), filtered, and the filtrate adjusted to pH 7 with 2 M-hydrochloric acid. The resulting mixture was filtered and the solid residue was dissolved in 2 M-hydrogen chloride in methanol at 0°. The solvent was evaporated and the solid residue was crystallised from methanol-ethyl acetate to give 3-(p-carboxyphenyl)-2-(2-dimethylaminoethylthio)quinoline hydrochloride, m.p. 246°-7°.

Workup

  1. customat 0°-5°
  2. filtrationfiltered
  3. filtrationThe resulting mixture was filtered
  4. dissolutionthe solid residue was dissolved in 2 M-hydrogen chloride in methanol at 0°
  5. customThe solvent was evaporated
  6. customthe solid residue was crystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-3c8c223b56da401aaba834c305c9ee9c
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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