Reaktion #58899

Reaktionsgleichung

4-fluoroaniline

ethyl formate

ethanol

Toluenesulfonylmethyl isocyanide

→

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

Ausbeute 85.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hrs
2. 2
   Temperaturwith heating
3. 3
   Temperaturunder reflux
4. 4
   EinengenThe reaction mixture was concentrated
5. 5
   workup.ADDITIONpoured into water
6. 6
   FiltrationThe precipitated solids were collected by filtration
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried

Vorschrift

A mixture of 4-fluoroaniline (11.1 g), ethyl formate (25.0 g) and ethanol (150 ml) was stirred at 65° C. for 2 hrs. Toluenesulfonylmethyl isocyanide (23.4 g) was added to the reaction mixture and the mixture was stirred for 2 hrs. with heating under reflux. The reaction mixture was concentrated and poured into water. The precipitated solids were collected by filtration, washed with water and dried to give ethyl 1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (19.8 g, 85%). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 114-115° C.

Quelle