Ammonium Chloride → HCID 67099285, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-nitro-benzonitrile (913 mg, 5.00 mmol) in MeOH (10 ml) is added powdered sodium methoxide (135 mg, 2.50 mmol) at room temperature. The solution is stirred at 65° C. for one day. Then ammonium chloride (294 mg, 5.5 mmol) is added and the mixture is refluxed for another day. The mixture is cooled to room temperature and the solvent removed in vacuo to give the crude 2-chloro-5-nitro-benzamidine hydrochloride, which is dissolved in THF (20 ml) and water (2 ml). This solution is transferred to a quartz reaction vessel (20 ml) and 2-bromoacetophenone (800 mg, 4 mmol) and potassium hydrogencarbonate (1.5 g, 15 mmol) are added. The reaction vessel is then placed into the cavity of a microwave reactor (Emrys optimizer) and irradiated for 15 minutes at 120° C. After the mixture is cooled to room temperature, the solvent is evaporated and the residue is dissolved in EtOAc (50 ml). The organic solution is washed with water (30 ml) and brine (30 ml), dried over MgSO4 and concentrated to give a crude dark oil, which is chromatographed (EtOAc/DCM=1/50) to give 2-(2-chloro-5-nitro-phenyl)-5-phenyl-1H-imidazole as a red solid.

Provenance & Evidence