Dimethyl Sulfate → 2-(4-Chloro-1H-pyrrol-2-YL)acetonitrile

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Reaction Steps

An aqueous solution of 114.0 g. of the product of Example VI is converted into the free base form by addition of 10% aqueous sodium hydroxide solution. The solid that is thus precipitated is filtered, washed with water and dried to give 67.1 g. (0.364 mole) of free base. The free base is dissolved in 350 ml. of dry dimethyl sulfoxide and stirred in an ice bath while 45.9 g. (0.364 mole) of dimethyl sulfate is added dropwise. The whole is then stirred for a half hour and warmed to room temperature, whereupon 20.0 g. (0.41 mole) of freshly ground and dried sodium cyanide is added all at once. After the resulting solution has been stirred for 2 hours at ambient temperature, it is poured onto ice and this aqueous solution is extracted four times with 250 ml. of diethyl ether. The combined ether extracts are washed successively with brine, 3N hydrochloric acid solution, aqueous sodium bicarbonate solution, and brine, and are dried over sodium sulfate. Evaporation of the ether yields 4-chloropyrrole-2 -acetonitrile as a brown oil.

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