Lawesson's reagent → HCID 45088409, compound

Participants

Reaction Steps

Lawesson's reagent (Tokyo Kasei Kogyo) (1.54 g, 3.8 mmols) was added to a benzene (25 ml) solution of the 2-((2S)-1-methyl-5-oxopyrrolidin-2-yl)ethanenitrile (1.05 g, 7.6 mmols), and the mixture was heated for 2 hours under reflux. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 60 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2S)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (941 mg, 80.6%): IR νmax (film) cm−1: 2246. 1H-NMR (CDCl3)δ: 4.20-4.10 (1H, m), 3.30 (3H, s), 3.25-2.98 (2H, m), 277 (1H, dd, J=17.0, 4.9 Hz), 2.68 (1H, dd, J=17.0, 6.6 Hz), 2.50-2.36 (1H, m), 2.06-1.94 (1H, m). MS m/z: 154 (M+), 114 (100%). HRMS: Calcd. for C7H10N2S: 154.0565 (M+). Found: 154.0561 (M+).

Provenance & Evidence