Potassium Carbonate → 2-(4-Nitrophenylthio)quinoline

HRID 55094

Reaction equation

HRID 55094 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 158094-Nitrobenzenethiol

Product 1

HCID 189716432-(4-Nitrophenylthio)quinolineYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloroquinoline (0.12 moles, 20.0 g), 4-nitrothiophenol (0.13 moles, 20.8 g), and potassium carbonate (0.13 moles, 18.5 g) were dissolved in 800 ml ethanol and stirred at room temperature for 1.5 hr. The mixture was filtered and the solid washed with ethanol. The solid was dissolved with ethyl acetate, washed with water, dried over sodium sulfate and concentrated to yield 2-(4-nitrophenylthio)quinoline 26.0 g, 77%. Mass Spec (FD) 282. Calculated for C15H10N2O2S: C, 63.82, H 3.57; N, 9.92. Found: C, 63.55, H 3.59; N, 9.71.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid washed with ethanol
  3. dissolutionThe solid was dissolved with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b51c3400761410e99d3cccc7aceea58
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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