Dimethylformamide → HCID 18680816, compound

HRID 1699630Notes

Reaction equation

HRID 1699630 reaction equation
CN(C)C=O.[N+:6]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1)([O-:8])=[O:7].C(=O)(O)[O-].[Na+].[CH3:22][C:23]1[NH:24][C:25]2[CH:31]=[C:30]([C:32](=[O:41])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH:29]=[CH:28][C:26]=2[N:27]=1>O.C(Cl)(Cl)Cl>[CH3:22][C:23]1[N:27]([CH2:13][C:12]2[CH:15]=[CH:16][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)[C:26]2[CH:28]=[CH:29][C:30]([C:32](=[O:41])[NH:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:31][C:25]=2[N:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 660114-Nitrobenzyl bromideHCID 516892Sodium BicarbonateHCID 18680895HCID 18680895, compound

Product 1

HCID 18680816HCID 18680816, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

N,N-dimethylformamide (10 ml), 4-nitrobenzyl bromide (3.24 g), and sodium bicarbonate (2.52 g) are added to 2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (3.56 g), and the solution is heated for two hours at 80° C. Chloroform and water are added to the reaction solution and layers are separated. After the organic layer is concentrated under reduced pressure, it is purified through silica gel column chromatography (eluate: ethyl acetate/methanol=4/1), and a mixture of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]benzimidazole is obtained. Further, the position isomers in this mixture are separated through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=85/15). Each is recrystallized in a mixed solvent of chloroform and diethylether, and thus, 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (1.37 g) (191) and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (1.19 g) (192) are obtained.

Workup

  1. customare separated
  2. concentrationAfter the organic layer is concentrated under reduced pressure, it
  3. customis purified through silica gel column chromatography (eluate: ethyl acetate/methanol=4/1)
  4. additiona mixture of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole

Sources & evidence

ORD record
ord-03a64fcf61844ce2896f1303e9dfb19f
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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