Reaction #2487390

Reaction equation

NaH

2,2′-biimidazole

DMF

methyl toluenesulfonate

→

1,1′-Dimethyl-2,2′-biimidazole

Yield 80.0%

Conditions

Workup

1. 1
   Otherover 30 min
2. 2
   workup.WAITwas continued for 1 h
3. 3
   workup.WAITat room temperature for 3 h
4. 4
   OtherThe solvent was removed by vacuum distillation
5. 5
   OtherThe dark residue was triturated with ether
6. 6
   Filtrationsuction filtered
7. 7
   Otherdried under vacuum
8. 8
   OtherThe product was purified by sublimation

Procedure

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%.

Source