Sodium Chloride → 1-[[4-(1H-Tetrazol-5-yl-methyl)phenoxy]methyl]cyclohexane

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(cyclohexylmethoxy)phenylacetonitrile (15 g, prepared in the preceding paragraph), sodium azide (21.3 g), ammonium chloride (17.4 g) and dimethylformamide (325 mL) was heated to 135° C. under a nitrogen atmosphere for 40 hours. The mixture was then cooled to room temperature and enough water was added to dissolve all the salts. The homogeneous solution was then poured into a separatory funnel containing saturated aqueous NaCl and ethyl acetate. After extraction of the aqueous phase with additional ethyl acetate, the combined extracts were washed with saturated brine solution, dried over MgSO4 and concentrated. The dark amber oil so obtained was treated with a little water and the resulting solid filtered off and crystallized from dichloromethane-diethyl ether mixture to afford 10.5 g (59% yield) of the title compound; m.p. 156°-158° C.

Provenance & Evidence