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

HRID 1893064ノート

反応式

HRID 1893064 の反応式
[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

参加物

5

反応物 4

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

生成物 1

HCID 101237781,1'-Dimethyl-1H,1'H-2,2'-biimidazole収率 80%

反応条件

温度
0 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-763347155cfe4e458c1907e401ec6dc0
出典データセット
uspto-grants-2013_08
特許番号
US08512534B2

反応ノート

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