5-CHLORO-2-METHYLTHIOBENZAMIDE synthesis

Yield:-

Reaction Conditions:

with Lawessons reagent in tetrahydrofuran at 23; for 1 h;

Steps:

4.2. Preparation of thioamides 2. General procedure

General procedure: Amides (1 mmol) and Lawesson's reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 1 h, or heated under reflux for 5 h in the case of the 4-nitro derivative. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO₃ (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous MgSO₄. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides as yellow solids (42-60%). 4-Nitrothioamide (2ff),³⁸ 4-cyanothiobenzamide (2gg)³⁹ and 3-cyanothiobenzamide (2hh),⁴⁰ 3-methoxythiobenzamide (2ii)⁴¹ have been previously reported.

References:

Mayhoub, Abdelrahman S.;Marler, Laura;Kondratyuk, Tamara P.;Park, Eun-Jung;Pezzuto, John M.;Cushman, Mark [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 510 - 520] Location in patent:experimental part