Iodoethane → m-(Ethylthio)aniline

HRID 245137Notes

Reaction equation

HRID 245137 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH3:17]>CN(C)C=O.O>[CH2:16]([S:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])[CH3:17]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 315773-Aminothiophenol

Product 1

HCID 74510m-(Ethylthio)anilineYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-aminobenzenethiol (5.0 g, 39.9 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (6.62 g, 47.9 mmol) and iodoethane (3.19 mL, 39.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes) to afford 3-(ethylthio)aniline (5.12 g, 84% yield). MS (m/z) 154.1 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3 times)
  2. washThe combined organic extracts were washed with brine (2 times)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1189293266f14b39bdc570b3758c04d7
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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