Water → 2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxaldehyde

HRID 487192Notes

Reaction equation

HRID 487192 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[CH:18]=[C:19](CO)[CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[C:24]1(C)C=CC=CC=1.[OH2:31]>[O-2].[O-2].[Mn+4]>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]2[C:18]([CH:24]=[O:31])=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 190942372-n-butyl-1-(2-chlorophenyl)methyl-6-hydroxymethyl-1H-benzimidazole

Product 1

HCID 190942612-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-7-carboxaldehydeYield 66%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

A suspension of 2-n-butyl-1-(2-chlorophenyl)methyl-6-hydroxymethyl-1H-benzimidazole (1 g, 3.04 mmol, prepared in Example 9(i)), toluene (500 mL) and activated manganese dioxide (4 g) was refluxed with a Dean-Stark water separator for 4 hours. The mixture was filtered hot, concentrated and the crude product was treated with celite in methylene chloride to afford, after concentration, a residue that crystallized. Recrystallization from hexane gave 0.65 g (66%) of 2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-benzimidazole-7-carboxaldehyde; mp 113.5°-115° C.

Workup

  1. filtrationThe mixture was filtered hot
  2. concentrationconcentrated
  3. additionthe crude product was treated with celite in methylene chloride
  4. customto afford
  5. concentrationafter concentration
  6. customa residue that crystallized
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-d0761cf341624c80aec6bb44c43bd7ec
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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