Carbon Disulfide → 1H-Pyrrole-1-carbodithioic acid phenylmethyl ester

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Reaction Steps

Pyrrole (1.34 g, 20 mmol) was added dropwise, with stirring, to a suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulphoxide (20 mL). Once the addition has ended, the resultant brown suspension was stirred for a further 30 min at room temperature before adding carbon disulphide (1.52 g, 20 mmol). The solution was stirred for a further 30 min at room temperature, and finally the benzyl chloride (2.53 g, 20 mmol) was added. After 1 h, water (20 mL) was added to the reaction mixture, followed by diethyl ether (20 mL). The organic phase was separated off, and then the aqueous phase was extracted twice, each time with 20 mL of diethyl ether. The combined organic phases were dried, using magnesium sulphate, and filtered, and the solvent was distilled off. The crude product was separated chromatographically, using 5% strength ethyl acetate in petroleum ether. The pure product was isolated in the form of a yellow oil at 50% yield (2.34 g).

Provenance & Evidence