Ethyl Acetate → 1-(4-Nitrophenylmethyl)-1H-imidazol-5-ylacetic acid methyl ester

Temperature

55 °C

To a solution of 1-(triphenylmethyl)-1H-imidazol-4-ylacetic acid methyl ester (23, 274 mg, 0.736 mmol) in acetonitrile (10 ml) was added 4-nitrobenzylbromide (159 mg, 0.736 mmol) and heated to 55° C. for 16 h. After this time, the reaction was cooled to room temperature, treated with ethyl acetate (20 ml) and the resulting precipitate was filtered. The filtrate was concentrated to dryness in vacuo and the residue was redissolved in acetonitrile (4 ml) and heated to 65° C. for 3 h. After this time, the reaction mixture was evaporated to dryness and combined with initial precipitate. This residue was dissolved in methanol (5 ml) and heated to reflux for 30 min. The resulting solution was evaporated in vacuo and the residue was purified by flash chromatography (2-5% methanol/methylene chloride gradient elution) to provide 16.

1. temperatureAfter this time, the reaction was cooled to room temperature
2. filtrationthe resulting precipitate was filtered
3. concentrationThe filtrate was concentrated to dryness in vacuo
4. dissolutionthe residue was redissolved in acetonitrile (4 ml)
5. temperatureheated to 65° C. for 3 h
6. customAfter this time, the reaction mixture was evaporated to dryness
7. dissolutionThis residue was dissolved in methanol (5 ml)
8. temperatureheated
9. temperatureto reflux for 30 min
10. customThe resulting solution was evaporated in vacuo
11. customthe residue was purified by flash chromatography (2-5% methanol/methylene chloride gradient elution)

ORD record

ord-3fc800d25cf44c47acb266e7f13f3efd

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05652257