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

HRID 417754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417754
[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

Komponenten

5

Edukt 4

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

Produkt 1

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

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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%.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d16489959e2340bc9f3fe64da65c777c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08092662B2

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