Reaction #640525

Reaction equation

4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine

4-(1H-Benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine

potassium carbonate

diiodomethane

3,4-dimethylphenol

→

title compound

4-[1-(3,4-Dimethylphenoxymethyl)-1H-benzimidazol-2-yl]-furazan-3-yl-N-(2-cyanoethyl)-amine

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   Dryingdried over sodium sulphate
3. 3
   FiltrationFiltration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel

Procedure

A suspension of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.15 g, 0.59 mmol, Example 6a), potassium carbonate (0.325 g, 2.36 mmol), diiodomethane (0.16 g, 0.59 mmol) and 3,4-dimethylphenol (0.072 g, 0.59 mmol) in DMF (5 ml) is stirred at room temperature for 16 hours. The reaction mixture is diluted with ethyl acetate, washed with water and dried over sodium sulphate. Filtration of the sodium sulphate, concentration of the filtrate under reduced pressure and chromatography of the residue on silicagel using hexane-ethyl acetate as eluent gives the title compound as a yellowish solid, m.p. 132-135° C.

Source