Water → N-[6-(2-Ethyl-phenylsulfanyl)-5-nitro-quinolin-8-yl]-acetamide

HRID 741575Notes

Reaction equation

HRID 741575 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[SH:11])[CH3:4].Cl[C:13]1[C:14]([N+:27]([O-:29])=[O:28])=[C:15]2[C:20](=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2.O>O1CCCC1>[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:13]1[C:14]([N+:27]([O-:29])=[O:28])=[C:15]2[C:20](=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4597198-Acetamido-6-chloro-5-nitroquinolineHCID 37343382-Ethylbenzenethiol

Product 1

HCID 19426748N-[6-(2-Ethyl-phenylsulfanyl)-5-nitro-quinolin-8-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.09 g of 60% in oil) is added to 2-ethylthiophenol (0.26 g) in tetrahydrofuran (10 mL) and stirred for 15 minutes. N-(6-chloro-5-nitro-quinolin-8-yl)-acetamide (Gilman H., et al., Journal of American Chemical Society, 1946;66:1577) (0.5 g) is added and the mixture stirred at room temperature for 12 hours. The mixture is added to water (150 mL) and extracted with ethyl acetate (3×100 mL). The extracts are washed with saturated brine (150 mL), dried over magnesium sulfate, filtered, and evaporated to leave an oil. The oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane to give the title compound as a yellow solid.

Workup

  1. stirringthe mixture stirred at room temperature for 12 hours
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe extracts are washed with saturated brine (150 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto leave an oil
  8. customThe oil is purified by chromatography on silica gel eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a91d3c90c13f4203850b3fb53c33c22f
Source dataset
uspto-grants-1996_09
Patent number
US05552411

Reaction notes

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