Dimethylformamide → HCID 86676842, compound

Participants

Reaction Steps

DMF (0.030 mL, 0.382 mmol) was added to a solution of 2-iodo-3-methylbenzoic acid (1.0 g, 3.82 mmol) and SOCl2 (0.279 mL, 3.82 mmol) in DCM (20 mL) at 0° C. After stirring 1 h at RT the solution was cooled to 0° C. DIPEA (2.0 mL, 11.45 mmol) followed by 2-(aminomethyl)pyridine (0.390 mL, 3.82 mmol) were added by slow addition and the solution was stirred at 0° C. After 1 h, the reaction was diluted with saturated ammonium chloride and the organics were removed. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with saturated ammonium chloride, water, saturated sodium bicarbonate, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material which was dissolved in toluene (20 mL). Lawesson's reagent (0.772 g, 1.908 mmol) was added and the reaction was refluxed for 12 h and then concentrated. The crude product was taken up in minimal DCM, and the product was precipitate out with diethyl ether to afford 2-iodo-3-methyl-N-(pyridin-2-ylmethyl)benzothioamide as a solid.

Provenance & Evidence