Nitric Acid → 1-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Participants

Reaction Steps

Dihydroxyacetone in dimeric form (23.35 g/0.129 mol) and potassium thioisocyanate (25.18 g/0.259 mol) are added in succession to a solution of 25 g (0.233 mol) of 4-(aminomethyl)benzonitrile in 100 ml of isopropanol, and then the mixture is placed in an ice bath and 20 ml of acetic acid are added dropwise. The reaction mixture is stirred at room temperature for 48 hours. A precipitate is obtained, which is filtered off, washed with 50 ml of isopropanol and then twice with 50 ml of H2O, and subsequently dried. Thus crystals are obtained, which are used directly in the following desulphurisation step: 13 g (0.059 mol) of the previously obtained crystals are placed in 140 ml of a dilute solution of 10% nitric acid in water. At 0° C., 0.1 g of sodium nitrite is added very slowly. Marked evolution of a brown gas is observed, and the mixture gradually becomes homogeneous. The reaction mixture is then stirred at room temperature for 3 hours and then filtered and extracted once with AcOEt. The aqueous phase is then rendered basic with a 5N sodium hydroxide solution, and subsequently extracted twice with AcOEt. The organic phase is washed with a saturated NaCl solution, and then dried over MgSO4. Evaporation in vacuo yields the title product.

Provenance & Evidence