Reaktion #159896

Reaktionsgleichung

4-Ethylaniline

ethyl oxoacetate

Potassium carbonate

isocyanomethyl 4-methylphenyl sulfone

→

product

ethyl 1-(4-ethylphenyl)-1H-imidazole-5-carboxylate

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturto reflux for 3 hours
3. 3
   TemperaturAfter cooling to room temperature
4. 4
   Filtrationthe reaction mixture was filtered through Celite
5. 5
   EinengenThe filtrate was concentrated in vacuo
6. 6
   workup.DISSOLUTIONdissolved in ethyl acetate
7. 7
   Waschenwashed with water
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigePurification via silica gel chromatography (Gradient: 0% to 33% ethyl acetate in heptane)

Vorschrift

4-Ethylaniline (2.08 mL, 16.6 mmol) and ethyl oxoacetate (50% solution in toluene, 3.30 mL, 16.6 mmol) were combined in ethanol (40 mL) and stirred at room temperature for 3 hours. Potassium carbonate (5.75 g, 41.6 mmol) and isocyanomethyl 4-methylphenyl sulfone (98%, 3.98 g, 20.0 mmol) were added and the reaction mixture was heated to reflux for 3 hours. After cooling to room temperature, the reaction mixture was filtered through Celite. The filtrate was concentrated in vacuo, dissolved in ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 0% to 33% ethyl acetate in heptane) afforded the product as a clear brown oil that solidified upon standing. Yield: 3.03 g, 12.4 mmol, 75%. LCMS m/z 245.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.24 (t, J=7.1 Hz, 3H), 1.29 (t, J=7.6 Hz, 3H), 2.73 (q, J=7.6 Hz, 2H), 4.21 (q, J=7.1 Hz, 2H), 7.27 (br AB quartet, JAB=8.6 Hz, ΔνAB=24 Hz, 4H), 7.66 (d, J=1.1 Hz, 1H), 7.85 (d, J=1.1 Hz, 1H).

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