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

Participants

Reaction Steps

Pyrrole (1.34 g, 20 mmol) was added dropwise to a stirred suspension of sodium hydride (0.48 g, 20 mmol) in dimethyl sulfoxide (20 mL). On completion of addition the resulting brown solution was stirred at room temperature for 30 minutes before the addition of carbon disulfide (1.52 g, 20 mmol). The solution was allowed to stir at room temperature for a further half hour and benzyl chloride (2.53 g, 20 mmol) added. Water (20 mL) was added after 1 hour followed by diethyl ether (20 mL). The organic layer was separated and the aqueous layer extracted with diethyl ether (2×20 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent removed. The crude product was chromatographed using 5% ethyl acetate in petroleum spirits to isolate the product as a yellow oil (2.34 g, 50%). 1H-nmr (CDCl3) δ 4.60 (2H), 6.30 (2H), 7.40 (5H), 7.70 (2H). 13C-nmr (CDCl3) δ 41.7, 114.2, 120.6, 128.0, 128.8, 129.4, 135.0, 189.0.

Provenance & Evidence