Potassium Iodide → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

温度

25 °C

To a stirred solution of N-hydroxy-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (1.00 g, 3.73 mmol) in acetonitrile (60 mL), were added cesium carbonate (2.55 g, 7.83 mmol), potassium iodide (310 mg, 1.86 mmol) and 2-bromo-4-bromomethyl-thiazole (1.05 g, 4.10 mmol). The resulting suspension was stirred at 25° C. for 6 h. The suspension was filtered, the solids washed with ethyl acetate and dichloromethane and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), washed with water, dried over MgSO4 concentrated in vacuo. Purification on silica gel afforded N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as an oil that solidified on standing after 2 days [1.49 g, yield 94%; HPLC/MS: m/z=425 (M+H); logP(HCOOH)=3.55].

1. filtrationThe suspension was filtered
2. washthe solids washed with ethyl acetate and dichloromethane
3. concentrationthe filtrate was concentrated in vacuo
4. dissolutionThe residue was dissolved in dichloromethane (50 mL)
5. washwashed with water
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customPurification on silica gel

ORDレコード

ord-873ede488f7647f9a741175586b90f1d

出典データセット

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08466176B2