Thiophenol → HCID 67520293, compound

HRID 1925258Notes

Reaction equation

HRID 1925258 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:18]1([SH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[S:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 67520293HCID 67520293, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-6,7-dimethoxy-quinoline (214 mg, 0.96 mmol) in EtOH (10 mL) and H2O (10 mL), was added KOH (107 mg, 1.44 mmol). The solution was stirred in a 100° C. bath. Then thiophenol (148 μL, 1.44 mmol) was added. The reaction was stirred at 100° C. for 1 h. The solvent was removed by rotary evaporation. The resulting residue was worked up with water and extracted with EtOAc 3×. The combined organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel prep-TLC with 100% EtOAc to give the titled compound. MS (ESI, pos. ion) m/z: 298.1 (M+1).

Workup

  1. stirringThe reaction was stirred at 100° C. for 1 h
  2. customThe solvent was removed by rotary evaporation
  3. extractionextracted with EtOAc 3×
  4. washThe combined organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel prep-TLC with 100% EtOAc

Sources & evidence

ORD record
ord-703890bbc0cc48a8846a0c63234e4427
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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