Iodoethane → m-(Ethylthio)aniline

HRID 435744Notes

Reaction equation

HRID 435744 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH2:11](I)[CH3:12].O1CCOCC1>C(OCC)C>[CH2:11]([S:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])[CH3:12]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 315773-Aminothiophenol

Product 1

HCID 74510m-(Ethylthio)anilineYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 25 grams (0.193 mole; M.W. 125.19) of 3-aminothiophenol in 200 ml. of 5N sodium hydroxide was added, dropwise, over a period of 1 hour, a solution of 29.9 grams (0.193 mole) of ethyl iodide in 50 ml. of 1,4-dioxane. The resulting suspension was allowed to stir at room temperature for 1 hour, 200 ml. of ethyl ether were then added, and stirring was continued for an additional 30 minutes. The ether layer was separated, washed with a saturated aqueous solution of sodium bisulfite, dried over Na2SO4, and evaporated in vacuo to yield 28.10 grams of m-ethylthioaniline.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 30 minutes
  3. customThe ether layer was separated
  4. washwashed with a saturated aqueous solution of sodium bisulfite
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ace8df1d55534298a966697c2d78d1a0
Source dataset
uspto-grants-1977_02
Patent number
US04006161

Reaction notes

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