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

HRID 1433503Notes

Reaction equation

HRID 1433503 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-f9141b74442440e68235fbd6a4f2907c
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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