tert-Butyldimethylsilyl chloride → HCID 136200580, compound

Participants

Reaction Steps

To a stirred solution of 2-hydroxy-4-morpholin-4-yl-benzamide (102 mg; 0.46 mmol) and t-butyldimethylsilyl chloride (73 mg; 0.48 mmol) in dry tetrahydrofuran (4 mL) was added Hunig's base (0.084 mL; 0.48 mmol) via syringe at room temperature under a nitrogen atmosphere. After stirring at room temperature for 4 hours, Lawesson's reagent was added (117 mg; 0.28 mmol) in one portion and the resulting solution was stirred for 16 hours. Benzyl trimethyl ammonium fluoride (1.84 mmol) then was added and stirring was continued for 2 hours longer. The reaction was concentrated at reduced pressure, and the residue re-dissolved in EtOAc (10 mL) and washed with water, 10% citric acid, 5% NaHCO3, and brine then dried (Na2SO4), filtered and concentrated in vacuo. The residue was then recrystallized from EtOAc/hexanes to provide the thioamide as a yellow solid (31 mg; 28%).

Provenance & Evidence