Hydrochloric Acid → 1-Dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene

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Reaction Steps

By using a method similar to that described in Example 35, but starting from 1-(4-fluorophenyl)-3-dimethylamino-2-propen-1-one (10 g), phosphorus oxychloride (4.76 cc), thiophenol (5.57 cc) and sodium cyanoborohydride (1.92 g), a residue is obtained which is taken up in chloroform. The solution is then adjusted to pH 10 by adding a concentrated aqueous solution of sodium hydroxide. The organic phase is separated and then the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressured (2.7 kPa) at 30° C. A residue is obtained which is dissolved in isopropanol (30 cc). A 3N solution (12 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The solid which precipitates is separated off by filtration and recrystallised from isopropanol (30 cc). In this way 1-dimethylamino-3-(4-fluorophenyl)-3-phenylthio-2-propene (E) hydrochloride (3.3 g) is obtained in the form of a white solid melting at 160° C.

Provenance & Evidence