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

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].

1. stirringthe mixture was stirred for 72 h at room temperature
2. waitat 70° C. for 3.5 h
3. filtrationThe reaction mixture was filtered
4. washthe insolubles washed with acetone and methanol
5. concentrationthe filtrate concentrated in vacuo
6. additiondiluted in ethyl acetate (50 mL)
7. washwashed with water (2×30 mL)
8. dry with materialdried over MgSO4
9. concentrationconcentrated to dryness in vacuo
10. customPurification of the residue on silica gel

ORD record

ord-47585d06c39b4e3480179390214b866f

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08981111B2