Reaktion #821668

Reaktionsgleichung

1-benzyl-1H-imidazole

triethylamine

3-(methoxycarbonyl)benzoic acid

thionyl chloride

→

title compound

Ausbeute 85.2%

Methyl 3-[(1-benzyl-1H-imidazol-2-yl)carbonyl]benzoate

Ausbeute 85.2%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 1 h
2. 2
   TemperaturThe mixture was cooled
3. 3
   Einengenconcentrated in vacuo and to the residue
4. 4
   workup.ADDITIONwas added toluene
5. 5
   EinengenThis solution was concentrated in vacuo and to the residue
6. 6
   TemperaturThe reaction mixture was heated
7. 7
   Temperaturat reflux for 18 h
8. 8
   Temperaturcooled
9. 9
   Einengenconcentrated in vacuo
10. 10
    workup.ADDITIONTo the residue was added ethyl acetate
11. 11
    Waschenthe solution was washed with water and saturated aqueous sodium hydrogen carbonate solution
12. 12
    FiltrationThe organic phase was filtered through silica
13. 13
    Wascheneluting with ethyl acetate
14. 14
    Einengenthe filtrate was concentrated in vacuo

Vorschrift

A solution of 3-(methoxycarbonyl)benzoic acid (2.53 g, 14.0 mmol) in thionyl chloride (7.17 ml, 98.30 mmol) was heated at reflux for 1 h. The mixture was cooled and concentrated in vacuo and to the residue was added toluene. This solution was concentrated in vacuo and to the residue was added anhydrous acetonitrile (24 ml), 1-benzyl-1H-imidazole (2.22 g, 14.0 mmol) and triethylamine (2.35 ml, 16.9 mmol). The reaction mixture was heated at reflux for 18 h and then cooled and concentrated in vacuo. To the residue was added ethyl acetate and the solution was washed with water and saturated aqueous sodium hydrogen carbonate solution. The organic phase was filtered through silica, eluting with ethyl acetate, and the filtrate was concentrated in vacuo to give the title compound (3.82 g).

Quelle