Potassium Hydroxide → S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate

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Reaction Steps

Powdered potassium hydroxide (3.3 g), 5.2 g of S-methyl-N-hydroxythioacetimidate, 0.1 g dicyclohexyl-18-crown-6, and 200 ml of benzene were stirred at room temperature for 0.5 hr. Then 8.0 g of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride was added slowly at 28° C. The reaction temperature was held at 28°-32° C. with external cooling. The mixture was stirred for 1 hr., and then was washed with water until neutral. After drying (MgSO4), the solution was concentrated in vacuo, and the residue was recrystallized from diisopropyl ether to give 9.0 g (76 percent yield) of S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)carbamoyloxy]Thioacetimidate, m.p. 68°-70° C.

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