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

HRID 7125

Reaction equation

HRID 7125 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-50f12f9a7e5d407b848aeee13aedd1a7
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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