Water → 1-(4-chlorobutyl)-2-phenyl-1H-benzimidazole

HRID 218045

Reaction equation

HRID 218045 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]I.O>CN(C)C=O>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][N:11]1[C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 128552-PhenylbenzimidazoleHCID 825271-Chloro-4-iodobutane

Product 1

HCID 269666231-(4-chlorobutyl)-2-phenyl-1H-benzimidazoleYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (12.88 mmol) of 2-phenyl-benzimidazole was dissolved in 30 ml of N,N-dimethylformamide, and 5.3 g (38.6 mmol) of K2CO3 and 2.0 ml (16.7 mmol) of 1-chloro-4-iodobutane were added to the resulting solution, followed by mixing the mixture at a room temperature for 10 hours. The reactant was combined with 100 ml of water and extracted with ethylacetate (70 ml×5) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (n-hexane/ethylacetate=2/1) to obtain 3.5 g (yield 96%) of the title compound.

Workup

  1. additionby mixing the mixture at a room temperature for 10 hours
  2. extractionextracted with ethylacetate (70 ml×5)
  3. washbeing washed with water
  4. dry with materiala sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-bcb62fb3cf794486aa6c3d206bc9a82f
Source dataset
uspto-grants-2012_06
Patent number
US08198307B2

Linked notes

Loading…