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

Participants

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine (4.08 g, 19.7 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (4.01 g, 21.7 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.5 g, 41.4 mmol) and potassium iodide (327 mg, 1.97 mmol). After stirring at room temperature for 51 h, potassium iodide (5.90 g, 35.5 mmol) was added and the mixture was stirred for 72 h at room temperature then at 70° C. for 3.5 h. The reaction mixture was filtered, the insolubles washed with acetone and methanol, and the filtrate concentrated in vacuo, diluted in ethyl acetate (50 mL), washed with water (2×30 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification of the residue on silica gel afforded 4-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [1.54 g, yield 23%; HPLC/MS: m/z=320 (M+H); log P(HCOOH)=0.22].

Provenance & Evidence