1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropane-1-carbothioamide

Participants

Reaction Conditions

Reaction Steps

1-Phenylcyclopropanenitrile (1-1, 10.0 g, 69.8 mmol) and sodium hydrosulfide hydrate (0.98 g, 17.5 mmol) were mixed in a 350 mL glass bomb and dissolved in 50 mL anhydrous EtOH. The resulting solution was cooled to −20° C. and a stream of H2S was bubbled through the mixture for 30 min. The bomb was sealed and heated to 90° C. for 2 days. The dark mixture was cooled to −25° C. and N2 was bubbled through for 1 h. The reaction mixture was diluted with H2O (50 mL) and extracted with Et2O (3×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The crude thioamide was triturated with hexanes to provide pure 1-phenylcyclopropanecarbothioamide (1-2) as a white solid.

Provenance & Evidence