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TCI Practical Example: Conversion of Carbonyl Group into Thiocarbonyl Group using Lawesson's Reagent

We are proud to present the conversion of carbonyl group to thiocarbonyl group using Lawesson's reagent.

Conversion of Carbonyl Group into Thiocarbonyl Group using Lawesson's Reagent

Used Chemicals

Procedure

To a solution of Lawesson's reagent (2.38 g, 5.88 mmol) in dichloromethane (42 mL), 2-pyrrolidone (1.0 g, 11.75 mmol) in dichloromethane (42 mL) was added at room temperature under N2 atmosphere. After stirring the reaction solution for 2 hours, the solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate = 9:1 - 6:4), giving pyrrolidine-2-thione as a white solid (0.79 g, 66%).

Experimenter’s Comments

The reaction was carried out in the fume hood due to the bad smell of Lawesson’s reagent.
The reaction mixture was monitored by TLC (hexane:ethyl acetate = 3:2, Rf = 0.28).

Analytical Data

pyrrolidine-2-thione

1H NMR (400 MHz, CDCl3); δ 8.61 (brs, 1H), 3.61 (t, 2H, J = 8.0 Hz), 2.86 (t, 2H, J = 8.0 Hz), 2.20-2.12 (m, 2H).

13C NMR (101 MHz, CDCl3); δ 205.83, 49.66, 43.21, 22.91.

Lead Reference

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