Sodium hydride → 2-(Dimethylcarbamoylmethylthio)-3-phenylquinoline

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Reaction Steps

3-Phenylquinolin-2-thione (4.74 g.; see Example 6) was added in portions to a well-stirred suspension of sodium hydride (1.06 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (25 ml.) at 0°-5°. After all the hydrogen gas had evolved, 2-chloro-N,N-dimethylacetamide (2.19 g.) was added and the mixture was heated at 80°. for 2 hr. The reaction mixture was then poured into water (300 ml.) and extracted with ethyl acetate (4×50 ml.). The ethyl acetate extract was washed with water (50 ml.) and then dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on basic alumina (70 g. of Brockmann Grade III), eluted with increasing concentrations of chloroform in petroleum ether. The eluate obtained with 20% v/v chloroform in petroleum ether was evaporated. The residual solid was crystallised from ethyl acetate-petroleum ether to give 2-(dimethylcarbamoylmethylthio)-3-phenylquinoline, m.p. 86°-9°.

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