Benzimidazole → 1-propyl-1h-benzimidazole

HRID 1970687Notes

Reaction equation

HRID 1970687 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH3:19]>CN(C)C=O>[CH2:17]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 336431-Iodopropane

Product 1

HCID 7387691-propyl-1h-benzimidazoleYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.0 g benzimidazole, 3.5 g potassium carbonate, 4.3 g 1-iodopropane and 20 ml N,N-dimethylformamide. The mixture was heated to 45 C under nitrogen for 16 hours and then quenched with 30 ml water and the product was extracted with ethyl acetate. Following removal of the solvent, the product was purified by silica gel chromatography using 66% ethyl acetate in hexane. The brown oil was again purified by silica gel chromatography using ethyl acetate, giving a slightly yellow oil 1.5 g.

Workup

  1. temperatureThe mixture was heated to 45 C under nitrogen for 16 hours
  2. customquenched with 30 ml water
  3. extractionthe product was extracted with ethyl acetate
  4. customremoval of the solvent
  5. customthe product was purified by silica gel chromatography
  6. customThe brown oil was again purified by silica gel chromatography

Sources & evidence

ORD record
ord-311e1294605a4a09bb30f0483c0dec68
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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