Iodoethane → 2-(Ethylthio)aniline

HRID 1816234Notes

Reaction equation

HRID 1816234 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][C:10](C)([O-])C.[K+].C(I)C>C(O)C>[CH2:9]([S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1])[CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 87132-AminothiophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 101490092-(Ethylthio)anilineYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Aminothiophenol (5.0 g, 40 mmol, Lancaster Synthesis Inc., Windham, N.H.) was stirred in dry ethanol (100 mL) and cooled in an ice bath. Potassium t-butoxide (4.5 g, 40 mmol) was added portionwise over 15 minutes and the mixture was stirred for an additional 45 minutes. Ethyl iodide (3.3 mL, 41 mmol) was added dropwise over 15 minutes and the mixture was allowed to warm to room temperature and stirred for 45 minutes. The mixture was filtered and the filtrate evaporated to dryness in vacuo. The resulting residue was treated with dichloromethane (100 mL) and filtered and the resulting filtrate was evaporated to dryness in vacuo to give 2-(ethylthio)aniline (5.2 g).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 45 minutes
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness in vacuo
  5. additionThe resulting residue was treated with dichloromethane (100 mL)
  6. filtrationfiltered
  7. customthe resulting filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-7bf821f9e11f4438a6614956ff948d7a
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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