Hydrochloric Acid → HCID 13200283, compound

HRID 1903223Notes

Reaction equation

HRID 1903223 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[H-].[Na+].[H][H].[Cl:12][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[ClH:12].[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][S:6][C:13]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 25798Captamine Hydrochloride2×HCID 516892Sodium BicarbonateHCID 13200202HCID 13200202, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13200283HCID 13200283, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-Dimethylaminoethanethiol hydrochloride (0.88 g.) was added to a suspension of sodium hydride (1.1 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (50 ml.) at 0°-5°. When all the hydrogen had evolved, a solution of 2-chloro-3-p-hydroxyphenylquinoline (1.6 g.) in dimethylformamide (10 ml.) was added and the mixture was stirred at ambient temperature for 16 hr. Additional 2-dimethylaminoethanethiol hydrochloride (0.32 g.), followed by a suspension of sodium hydride (0.4 g. of a 50% w/w dispersion in mineral oil), was added and the mixture was heated at 65° for 2 hr. The mixture was then cooled to ambient temperature, poured into water (500 ml.), and adjusted to pH 2 with 2 M-hydrochloric acid. The solution was then adjusted to pH 8 with saturated sodium bicarbonate solution and extracted with ethyl acetate (2×100 ml.). The ethyl acetate extract was washed with water (2×50 ml.) and dried (MgSO4 ). The solvent was evaporated, the residue was dissolved in diethyl ether (200 ml.), and ethereal hydrogen chloride was added. The solvent was evaporated, and the residue was crystallised from ethanol-diethyl ether to give 2-(2-dimethylaminoethylthio)-3-(p-hydroxyphenyl)quinoline hydrochloride, m.p. 220°-2°.

Workup

  1. customat 0°-5°
  2. additionof a 50% w/w dispersion in mineral oil), was added
  3. temperaturethe mixture was heated at 65° for 2 hr
  4. temperatureThe mixture was then cooled to ambient temperature
  5. extractionextracted with ethyl acetate (2×100 ml.)
  6. extractionThe ethyl acetate extract
  7. washwas washed with water (2×50 ml.)
  8. dry with materialdried (MgSO4 )
  9. customThe solvent was evaporated
  10. dissolutionthe residue was dissolved in diethyl ether (200 ml.)
  11. additionethereal hydrogen chloride was added
  12. customThe solvent was evaporated
  13. customthe residue was crystallised from ethanol-diethyl ether

Sources & evidence

ORD record
ord-bd7143e3ebb84210b23ad9a9d9e5d73a
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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