Dimethylformamide → 1,1'-Dimethyl-1H,1'H-2,2'-biimidazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,2′-biimidazole (Fieselmann, B. F., et al. Inorg. Chem. 17, 2078(1978)) (4.6 g, 34.3 mmoles) in 100 mL dry DMF in a 250 ml round bottom flask cooled in an ice/water bath was added in portions NaH (60% in mineral oil, 2.7 g, 68.6 mmoles). After the solution was stirred at 0° C. for one hour under N2, methyl toluenesulfonate (10.3 mL, 68.6 mmoles) was added in small portions using a syringe over 30 min. The stirring of the solution in the ice/water bath was continued for 1 h and then at room temperature for 3 h. The solvent was removed by vacuum distillation. The dark residue was triturated with ether and then suction filtered and dried under vacuum. The product was purified by sublimation. Yield: 80%.

Provenance & Evidence