Iodoethane → m-(Ethylthio)aniline

HRID 554249Notes

Reaction equation

HRID 554249 reaction equation
[H-].[Na+].O1CC[CH2:5][CH2:4]1.[NH2:8][C:9]1[CH:10]=[C:11]([SH:15])[CH:12]=[CH:13][CH:14]=1.ICC>O.CN(C)C=O>[CH2:4]([S:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[NH2:8])[CH3:5]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 315773-Aminothiophenol

Product 1

HCID 74510m-(Ethylthio)anilineYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 2.3 g) was suspended in a mixed solvent of tetrahydrofuran (35 mL) and N,N-dimethylformamide (15 mL), and 3-aminobenzenethiol (5.0 g) was added dropwise at room temperature. The mixture was stirred at the same temperature for 5 min, iodoethane (6.86 g) was added, and the mixture was stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a yellow oil (yield 5.0 g, 82%).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringthe mixture was stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-2c60184c0db944ea8890c4c349e0bfd5
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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