Potassium Iodide → 4-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine (1.60 g, 5.73 mmol), 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (937 mg, 6.30 mmol) and potassium iodide (951 mg, 5.73 mmol) in acetonitrile (15 mL) at 0° C. was added 1,5-diazabicyclo(4.3.0)non-5-ene (1.44 mL, 12.0 mmol). The mixture was stirred 10 min at 0° C., then overnight at room temperature. After dilution of the reaction mixture with water and extraction with ethyl acetate, the combined organic layers were dried over MgSO4, concentrated in vacuo, and the residue purified by reverse phase HPLC to afford 4-[({[(3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [16 mg, yield 0.7%].

Provenance & Evidence