Reaction #640523

Reaction equation

diiodomethane

4-(1H-benzimidazol-2-yl)-furazan-3-ylamine

potassium carbonate

4-fluorophenol

→

title compound

4-[1-(4-Fluorophenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-ylamine

Conditions

Workup

1. 1
   OtherEvaporation of the solvent under reduced pressure
2. 2
   Otherpartitioning of the resulting residue between water and ethyl acetate
3. 3
   Dryingby drying of the organic solution over sodium sulphate and chromatography of the residue

Procedure

To a solution of 4-(1H-benzimidazol-2-yl)-furazan-3-ylamine (0.10 g, 0.497 mmol) is added potassium carbonate (0.172 g, 1.24 mmol) followed by 4-fluorophenol (0.0557 g, 0.497 mmol) and diiodomethane (0.133 g, 0.497 mmol). The mixture is stirred over night. Evaporation of the solvent under reduced pressure and partitioning of the resulting residue between water and ethyl acetate followed by drying of the organic solution over sodium sulphate and chromatography of the residue gives the title compound as a colorless solid, m.p. 155-158° C.

Source