Reacción #1596043

Ecuación de reacción

2-(4-nitrophenyl)acetamide

1,3-dioxol-2-one

Eaton's Reagent

→

title compound

Rendimiento 25.0%

2-(4-nitrobenzyl)oxazole

Rendimiento 25.0%

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter this time, the reaction was cooled
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   SecadoThe combined organic layer was dried over anhydrous sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónthe filtrate was concentrated
6. 6
   OtroThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Procedimiento

A mixture of 2-(4-nitrophenyl)acetamide (1.0 g, 5.55 mmol), 1,3-dioxol-2-one (0.955 g, 11.10 mmol), and Eaton's Reagent (9.9 g, 34.97 mmol) was heated to 100° C. overnight under a nitrogen atmosphere. After this time, the reaction was cooled, diluted with ice water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.250 g, 25%). MW=204.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.26-8.18 (m, 2H), 8.05 (d, J=0.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.16 (s, 1H), 4.34 (s, 2H); APCI MS m/z 205 [M+H]+.

Fuente