Iodoethane → m-(Ethylthio)aniline

Participants

Reaction Steps

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.

Provenance & Evidence