Triethylamine → HCID 90021697, compound

Participants

Reaction Steps

To a solution of 5-chlorosalicylic acid (863 mg, 5.0 mmol, 1.0 eq.) in THF (3 mL) and water (4 mL), 1-hydroxybenzotriazole hydrate (1.01 g, 7.5 mmol, 1.5 eq.) was added. The resulting solution was stirred at r.t. for 30 minutes. Then 2-(2-isopropyl-1,3-thiazol-4-yl)ethanamine hydrochloride (1.03 g, 5.0 mmol, 1.0 eq.) in THF (3 mL) and NEt3 (1.39 mL, 10.0 mmol, 2.0 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.44 g, 7.5 mmol, 1.5 eq) in water (4 mL) were added in sequence. The resulting mixture was stirred at r.t. for 18 hours. The reaction mixture was poured in sat. aq. NaHCO3 (75 mL). The mixture was extracted with AcOEt (2×50 mL). The comb. org. phases were washed with 1M aq. HCl soln. (50 mL) and sat. aq. NaCl soln. (1×20 mL), dried over MgSO4, and concentrated in vacuo to give the desired amide as a brown oil. The product was used without further purification.

Provenance & Evidence