Hydrolysis of , -Diethylethanesulfenamide. (a) With Potassium Hydroxide in Methanol.-Ten grams of, -diethylethanesulf enamide (0.75 mole) was dissolved in 150 ml. of 1 N KOH in methanol. The solution was refluxed for 3 hr., at which time the absorption spectrum of a sample had stabilized with an ultraviolet absorption plateau in the region of 240-255 m/u. The solution was then distilled at atmospheric pressure. Fractions boiling at 65-67.5°were collected. They gave positive nitroprusside tests for disulfides,13 became cloudy when diluted with (13) E.
NOTES
VOL. 22When addition was complete (1 hr.), the reaction mixture was allowed to stand a t room temperature for 4 hr., and then poured into 500 ml. of ice water containing 50 g. of T\;H,CI. The aqueous layer was separated and extracted with 60 ml. of ether. The combined ethereal layers were washed with two 100 ml. portions of 20y0 NH4CI and then with brine. After drying over MgS04, the ether was removed and the product was distilled through an 8 cm. helix-packed column. The fraction boiling 99-100°/30 mm. was collected; 50.5 g. (81%). A sample which had been redistilled twice through a 20 cm. Widmer column had the following physical properties: b.p. 99-100°/30 mm., 85-85.5"/15 mm.; nY 1.4837; d25 0.9669. The I.R. spectrum in CCl, solution showed strong absorption a t 2.95 p and weak absorption at 4.5 p.
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