Sodium Azide → 1h-Benzimidazole-1-carboxylic acid,4-(azidomethyl)-,1,1-dimethylethyl ester

HRID 1352014Notes

Reaction equation

HRID 1352014 reaction equation
Br[CH2:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CC(C)=O.[I-].[Na+]>[N:19]([CH2:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

Product 1

HCID 207147611h-Benzimidazole-1-carboxylic acid,4-(azidomethyl)-,1,1-dimethylethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 4-(bromomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (1.08 g, 3.5 mmol), sodium azide (240 mg, 3.7 mmol), and sodium iodide (5 mg) in acetone (10 mL) was heated at reflux for 66 h. The solvent was evaporated and dichloromethane was added. The solution was washed with dilute aqueous sodium hydrogen carbonate, dried (Na2SO4), filtered and evaporated to give 4-(azidomethyl)benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester (800 mg, 84%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 66 h
  3. customThe solvent was evaporated
  4. additiondichloromethane was added
  5. washThe solution was washed with dilute aqueous sodium hydrogen carbonate
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8e30f8aa66e3416a8cd8c80c5df4f5b6
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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