Acetic Acid → [2-(2,3-dihydro-1H-imidazo-[1,2-a]benzimidazole-1-yl)ethyl]acetate

HRID 1886054Notes

Reaction equation

HRID 1886054 reaction equation
I[CH2:2][CH2:3][N:4]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5]1.[C:16]([OH:19])(=[O:18])[CH3:17].C1CCN2C(=NCCC2)CC1.CCOC(C)=O>C1(C)C=CC=CC=1>[N:4]1([CH2:3][CH2:2][O:19][C:16](=[O:18])[CH3:17])[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 151427111-N-(2-Iodoethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Product 1

HCID 131717530[2-(2,3-dihydro-1H-imidazo-[1,2-a]benzimidazole-1-yl)ethyl]acetateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the procedure of N. Ono, et al., Bull. Chem. Soc. Jpn., 51 (8), 2401 (1978), a solution of 1-N-(2-iodoethyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (2.20 g, 7.03 mmol), acetic acid (0.060 mL, 10.54 mmol) and DBU (1.57 mL, 10.54 mmol) in toluene (70 mL) was heated under reflux for 4 hours, cooled, and stirred at room temperature overnight. EtOAc (30 mL) was added and the mixture was washed with brine, dried (MgSO4), and concentrated to give 1.68 g (98%) of a brown solid. This material was used without further purification in the next step (hydrolysis).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. washthe mixture was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-183dd49ea79e42efab31e38196a6aede
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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