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Dimethylformamide → 2-Benzyl-1-(2,4-dichlorobenzyl)-5-ethoxycarbonylbenzimidazole

HRID 321965
Notes
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Reaction equation

HRID 321965 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:8]=1[CH2:9]Br.C(=O)(O)[O-].[Na+].[CH2:21]([C:28]1[NH:29][C:30]2[CH:36]=[C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:34]=[CH:33][C:31]=2[N:32]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.C(OCC)(=O)C>[CH2:21]([C:28]1[N:32]([CH2:9][C:8]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:7]=2[Cl:6])[C:31]2[CH:33]=[CH:34][C:35]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:36][C:30]=2[N:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 102213332-Benzyl-5-ethoxycarbonylbenzimidazoleHCID 109883732,4-Dichlorobenzyl bromide

Product 1

HCID 183154272-Benzyl-1-(2,4-dichlorobenzyl)-5-ethoxycarbonylbenzimidazoleYield 14%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

N,N-dimethylformamide (15 ml), 2,4-dichlorobenzyl bromide (4.45 g) and sodium bicarbonate (1.23 g) are added to 2-benzyl-5-ethoxycarbonyl-benzimidazole (2.37 g) (example 11) 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 2-benzyl-1-(2,4-dichlorobenzyl)-6-ethoxycarbonylbenzimidazole (0.49 g) and 2-benzyl-1-(2,4-dichlorobenzyl)-5-ethoxycarbonylbenzimidazole (0.52 g) is obtained. Separation and purification is performed using medium pressure silica gel column chromatography (eluate: hexane/ethyl acetate=1/4˜0/100).

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 2-benzyl-1-(2,4-dichlorobenzyl)-6-ethoxycarbonylbenzimidazole (0.49 g)

Sources & evidence

ORD record
ord-37e4acb619f94b49b322a0529da599c3
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211177B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes