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

HRID 72065Notes

Reaction equation

HRID 72065 reaction equation
[CH:1]1[NH:5][C:4]([C:6]2[NH:10][CH:9]=[CH:8][N:7]=2)=[N:3]C=1.[H-].[Na+].[C:13]1([CH3:24])C(S(OC)(=O)=O)=CC=CC=1.[CH3:25]N(C=O)C>>[CH3:25][N:7]1[CH:8]=[CH:9][N:10]=[C:6]1[C:4]1[N:5]([CH3:1])[CH:13]=[CH:24][N:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 90076Benzenesulfonic acid, 2-methyl-, methyl esterHCID 1014632,2'-Biimidazole

Product 1

HCID 101237781,1'-Dimethyl-1H,1'H-2,2'-biimidazoleYield 80%

Conditions

Temperature
0 °C

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%.

Workup

  1. customover 30 min
  2. waitwas continued for 1 h
  3. waitat room temperature for 3 h
  4. customThe solvent was removed by vacuum distillation
  5. customThe dark residue was triturated with ether
  6. filtrationsuction filtered
  7. customdried under vacuum
  8. customThe product was purified by sublimation

Sources & evidence

ORD record
ord-3634a42d04ae4811b7bc91de35b0a6af
Source dataset
uspto-grants-2014_09
Patent number
US08828204B2

Reaction notes

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