Potassium Iodide → HCID 86650745, compound

Participants

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-phenylmethanimine (3.90 g, 19.4 mmol) and 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (3.95 g, 21.3 mmol) in acetonitrile (50 mL) were added cesium carbonate (13.3 g, 40.7 mmol) and potassium iodide (322 mg, 1.93 mmol). After stirring at room temperature for 29 h, N-N-dimethylformamide (5 mL) was added and the mixture was further at room temperature for 72 h. The reaction mixture was filtered, the insolubles washed with acetone, and the filtrate concentrated in vacuo. Purification on silica gel afforded 4-[({[(1-methyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [1.09 g, yield 16%; HPLC/MS: m/z=314 (M+H); log P(HCOOH)=0.69].

Provenance & Evidence