Sodium Iodide → HCID 15675385, compound

HRID 1461269Notes

Reaction equation

HRID 1461269 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13].[I-].[Na+].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 36534711-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one2×

Product 1

HCID 15675385HCID 15675385, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In 30 ml of dimethylformamide were dissolved 1.5 g of the above 1:1 (approx.) mixture of Compound h and Compound h', 1.5 g (9.9 mmol) of sodium iodide and 5.0 g (76.3 mmol) of sodium azide and the solution was heated at 120° C. for 48 hours. After cooling, the solvent was distilled off and 50 ml of ethyl acetate was added to the residue. The insolubles were filtered off and the filtrate was washed twice with 5% aqueous sodium thiosulfate solution and, then, three times with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 1.38 g (98.9%) of 1-(2-azidoethyl)-2,3-dihydro-2-oxo-1H-benzimidazole (Compound i) as light yellow crystals.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. addition50 ml of ethyl acetate was added to the residue
  4. filtrationThe insolubles were filtered off
  5. washthe filtrate was washed twice with 5% aqueous sodium thiosulfate solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f74d634d08c41cd81e874e4c2c34ed1
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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