Potassium Carbonate → 2-(4-Nitrophenylthio)quinoline

HRID 2395350Notes

Reaction equation

HRID 2395350 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 70,842.297%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloroquinoline (0.12 moles, 20.0 g), 4-nitrothiophenol (0.13 mmoles, 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-4f25e650f8874b858d11c90003d982c4
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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