Sodium hydride → 1-(3,4-Dichiorobenzyl)-2-pyridin-2-yl-1H-benzoimidazole

HRID 963444

Reaktionsgleichung

Reaktionsgleichung von HRID 963444
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=1.[H-].[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Br>CN(C=O)C.O>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 708212-(2'-Pyridyl)benzimidazoleHCID 6397264-(Bromomethyl)-1,2-dichlorobenzene

Produkt 1

HCID 153762251-(3,4-Dichiorobenzyl)-2-pyridin-2-yl-1H-benzoimidazoleAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Pyridin-2-yl-lH-benzoimidazole (1.95 g, 0.01 mol) was dissolved in DMF (50 mL) under an atmosphere of nitrogen. Sodium hydride (60% dispersion in oil, 0.48 g, 0.012 mol) was then added. The reaction mixture was stirred at ambient temperature for 0.5 hour. 3,4-Dichlorobenzyl bromide (2.4 g, 0.01 mol) was then added. The mixture was stirred at 80° C. for a period of 4 hours. The mixture was cooled and diluted with water. The mixture was then extracted with ethyl acetate. The organic extract was washed with water twice then evaporated. The residue was triturated with a small amount of ethyl acetate/hexane. The solid was collected and crystallized from ethanolic hydrogen chloride. The solid was collected to give the title compound (1.3 g, 36.7% yield) as a mono-hydrochloride, light brown solid, m.p. 227°-229° C. Anal. Calcd. for Cl9Hl3Cl2N3-HCl: C, 58.41; H, 3.61; N, 10.76.. Found: C, 58.21; H, 3.54; N, 10.80. Mass spectrum (+FAB; [M+H]+) 354/356/358. 1H-NMR (DMSO-d6 ; 400 MHz) 8 8.78 (d, 1H), 8.52 (d, 1H), 8.15 (t, 1H), 7.9 (d, 1H), 7.77 (d, 1H), 7.65 (d, 2H), 7.54 (d, 1H), 7.48-7.52 (m, 2H), 7.23 (d, 1H), and 6.22 ppm (s, 2H).

Aufarbeitung

  1. stirringThe mixture was stirred at 80° C. for a period of 4 hours
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was then extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water twice
  6. customevaporated
  7. customThe residue was triturated with a small amount of ethyl acetate/hexane
  8. customThe solid was collected
  9. customcrystallized from ethanolic hydrogen chloride
  10. customThe solid was collected

Quellen und Nachweise

ORD-Eintrag
ord-66f230093170450a8e296d34fd904649
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763473

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