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

HRID 2256397

Reaction equation

HRID 2256397 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 153762251-(3,4-Dichiorobenzyl)-2-pyridin-2-yl-1H-benzoimidazoleYield 36.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Pyridin-2-yl-1H-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 C19H13Cl2N3.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) δ 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).

Workup

  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

Sources & evidence

ORD record
ord-3f310ab0353d415f946ba358c0647fcc
Source dataset
uspto-grants-1997_08
Patent number
US05654436

Linked notes

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