N-benzimidazolyl-1,2-propanediol → (1H-Benzimidazol-1-yl)acetaldehyde

HRID 747325

Reaction equation

HRID 747325 reaction equation
[N:1]1([CH:10](O)[CH:11]([OH:13])C)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I([O-])(=O)(=O)=O.[Na+]>O>[N:1]1([CH2:10][CH:11]=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 22018573N-benzimidazolyl-1,2-propanediolHCID 23667635Sodium periodate

Product 1

HCID 22018662(1H-Benzimidazol-1-yl)acetaldehydeYield 41.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The intermediate, N-benzimidazolyl-1,2-propanediol (0.66 g, 3.4 mmol) from above was dissolved in water (25 mL) and treated with sodium periodate (0.88 g, 4.1 mmol) with stirring for 1.5 hours. The solution was then extracted with dichloromethane, dried (MgSO4), filtered and concentrated to yield 2-(benzimidazol-1-yl)-ethanal (0.22 g, 1.4 mmol) which was used immediately without further purification in the next reaction.

Workup

  1. extractionThe solution was then extracted with dichloromethane
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-07e02f8835a44c29a64f8bdb57c39cac
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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