Sodium Sulfide → 7-Methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamide

HRID 387850Notes

Reaction equation

HRID 387850 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([C:12]([NH2:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[S-2:17].[Na+].[Na+].Br[C:21]1[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1>CN(C)C=O>[CH3:16][O:15][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([S:17][C:21]3[S:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][C:9]=1[C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 832222-Bromo-5-nitrothiopheneHCID 229364184-Chloro-7-methoxyquinoline-6-carboxamide

Product 1

HCID 229366247-Methoxy-4-(5-nitrothiophen-2-ylsulfanyl)quinoline-6-carboxamideYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-7-methoxyquinoline-6-carboxamide (1.18 g, 5.00 mmol) and sodium sulfide (1.20 g, 5.50 mmol) were heated and stirred in dimethylformamide (10 ml) at 60° C. for 3 hours. After cooling the reaction solution to room temperature, 2-bromo-5-nitrothiophene (1.25 g, 6.00 mmol) was added and the mixture was further heated and stirred at 60° C. for 1 hour. The reaction solution was returned to room temperature and then poured into ice water (50 ml), and the precipitated crystals were filtered out, washed with water and methanol and then blow-dried to obtain the title compound (700 mg, 1.94 mmol, 39%) as yellowish-brown crystals.

Workup

  1. temperaturethe mixture was further heated
  2. customwas returned to room temperature
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water and methanol
  5. customblow-dried

Sources & evidence

ORD record
ord-012fea1c2dd441b8acf2f1e449f0c021
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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