Sodium Iodide → 1-N-(2-Iodoethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

HRID 1886053Notes

Reaction equation

HRID 1886053 reaction equation
[Na+].[I-:2].CC(=O)CC.Cl[CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:14]2[CH2:13][CH2:12]1>CCOC(C)=O>[I:2][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:14]2[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6569Methyl Ethyl Ketone2×HCID 7619001-(2-chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Product 1

HCID 151427111-N-(2-Iodoethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of NaI (1.73 g, 11.57 mmol) and 2-butanone (20 mL) was heated under reflux for 30 minutes 1-N-(2-Chloroethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (1.70 g, 7.71 mmol) and additional 2-butanone (5 mL) were added and heating was continued for 5 hours. EtOAc (50 mL) was added and the mixture was filtered. The filtrate was washed with H2O, 10% sodium bisulfite (25 mL), saturated aqueous NaHCO3, dried (MgSO4) and concentrated to give 2.2 g (92%) of a light brown solid m.p. 101°-103° C.

Workup

  1. temperaturewas heated
  2. additionwere added
  3. temperatureheating
  4. filtrationthe mixture was filtered
  5. washThe filtrate was washed with H2O, 10% sodium bisulfite (25 mL), saturated aqueous NaHCO3
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d488baf2d824817987841efeb44cf76
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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