Dimethylformamide → HCID 18681168, compound

HRID 1699610Notes

Reaction equation

HRID 1699610 reaction equation
CN(C)C=O.[N+:6]([C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]Br)([O-:8])=[O:7].C(=O)(O)[O-].[Na+].[CH2:22]([O:24][C:25]([C:27]1[CH:36]=[CH:35][C:30]2[N:31]=[C:32]([CH3:34])[NH:33][C:29]=2[CH:28]=1)=[O:26])[CH3:23]>O.C(OCC)(=O)C>[CH2:22]([O:24][C:25]([C:27]1[CH:36]=[CH:35][C:30]2[N:31]([CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[N+:6]([O-:8])=[O:7])[C:32]([CH3:34])=[N:33][C:29]=2[CH:28]=1)=[O:26])[CH3:23]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 77569alpha-Bromo-2-nitrotolueneHCID 516892Sodium BicarbonateHCID 15185606HCID 15185606, compound

Product 1

HCID 18681168HCID 18681168, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N,N-dimethylformamide (15 ml), 2-nitrobenzyl bromide (1.59 g) and sodium bicarbonate (1.23 g) are added to 5-ethoxycarbonyl-2-methylbenzimidazole (1.00 g) and the solution is heated for one hour at 60° C. After adding ethyl acetate (70 ml) and water (70 ml) and separating the solution, the organic layer is washed with water three times and extraction is performed on the aqueous layer using ethyl acetate three times. By concentrating the obtained organic layer under reduced pressure, a mixture of 6-ethoxycarbonyl-2-methyl-1-(2-nitrobenzyl)benzimidazole and 5-ethoxycarbonyl-2-methyl-1-(2-nitrobenzyl)benzimidazole is obtained. Purification using medium pressure silica gel column chromatography (eluate: hexane/etlhyl acetate=1/4˜0/100) produced 6-ethoxycarbonyl-2-methyl-1-(2-nitrobenzyl)benzimidazole (83) (0.614 g) and 5-ethoxycarbonyl-2-methyl-1-(2-nitrobenzyl)benzimidazole (84) (0.259 g). 1H-NMR CDCl3, δ): 1.38 (3H, t, J=7.2 Hz), 2.56 (3H, s), 4.37 (2H, q, J=7.1 Hz), 5.84 (2H, s), 6.41 (1H, d, J=6.8 Hz), 7.44-7.53 (2H, m), 7.78 (1H, d, J=8.6 Hz), 7.88 (1H, s), 8.02 (1H, dd, J=8.3 and 1.5 Hz), 8.30 (1H, dd, J=7.9 and 1.5 Hz).

Workup

  1. customseparating the solution
  2. washthe organic layer is washed with water three times and extraction
  3. concentrationBy concentrating the obtained organic layer under reduced pressure
  4. additiona mixture of 6-ethoxycarbonyl-2-methyl-1-(2-nitrobenzyl)benzimidazole

Sources & evidence

ORD record
ord-57c87fcb3efc4a54987bb5b7470eebe5
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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