Benzimidazole → 1-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazole

HRID 2268506Notes

Reaction equation

HRID 2268506 reaction equation
I[CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:7]=2[CH2:6][CH2:5]1.[N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[NH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH3:16][O:15][C:14]1[C:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]=[CH:24]3)[CH2:10][CH2:9][C:8]=2[C:11]([O:21][CH3:22])=[C:12]([O:19][CH3:20])[C:13]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 10340Sodium CarbonateHCID 183485187-(2-Iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene

Product 1

HCID 183485591-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl]-1H-benzo[d]imidazoleYield 32.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-(2-iodoethyl)-1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cycloheptene (1.50 g), benzimidazole (443 mg), and sodium carbonate (760 mg) in DMF (15 ml) was stirred at 70° C. for 8 hr. The reaction mixture was diluted with water and extracted with combined solution of ethyl acetate and THF. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was diluted with diethylether and the resultant crystals were removed by filtration. The filtrate was concentrate in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2) and then with recrystallization from hexane-ethyl acetate to obtain the entitled compound (480 mg).

Workup

  1. extractionextracted with combined solution of ethyl acetate and THF
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. customdried
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted with diethylether
  6. customthe resultant crystals were removed by filtration
  7. concentrationThe filtrate was concentrate in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:2)
  9. customwith recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ad73347caa454111b59c1ad69d1b0a9c
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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