Tin tetrachloride → HCID 24700976, compound

To a solution of 1-(4-bromo-2-nitro-phenyl)-1H-imidazole (1.80 g; 6.72 mmol; 1 eq) in ethanol (90 mL) is added dehydrated tin chloride (7.58 g; 33.58 mmol; 5 eq). The reaction mixture is allowed to stir under reflux for 20 hours until completion of the reaction. The crude reaction mixture is then concentrated under vacuum. The resulting mixture is dissolved in water/ethyl acetate 1:2 (40 mL). The aqueous phase is basified until pH 9 is reached with solid hydrogen carbonate. The milky white aqueous phase is then extracted twice with ethyl acetate (2×100 mL). The combined organic phases are washed with brine (100 mL), dried over sodium sulfate and concentrated under vacuum to provide a beige powder. Purification by chromatography on silica gel (dichloromethane/methanol 97:3), afforded the title compound (1.47 g; 6.2 mmol; 92%) as a yellow powder.

1. temperatureunder reflux for 20 hours until completion of the reaction
2. customThe crude reaction mixture
3. concentrationis then concentrated under vacuum
4. dissolutionThe resulting mixture is dissolved in water/ethyl acetate 1:2 (40 mL)
5. extractionThe milky white aqueous phase is then extracted twice with ethyl acetate (2×100 mL)
6. washThe combined organic phases are washed with brine (100 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under vacuum
9. customto provide a beige powder
10. customPurification by chromatography on silica gel (dichloromethane/methanol 97:3)

ORD record

ord-532aac8195f841d7af56d70b2bc28a96

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513250B2