Ethyl Acetate → HCID 67211040, compound

HRID 452140Notes

Reaction equation

HRID 452140 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH:38]=[CH:37][C:23]2/[C:24](=[C:33](/[CH3:36])\[C:34]#[N:35])/[C:25]3[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=3[O:27][CH2:28][C:22]=2[CH:21]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([C:3]1[N:4]([CH2:19][C:20]2[CH:38]=[CH:37][C:23]3/[C:24](=[C:33](/[CH3:36])\[C:34]#[N:35])/[C:25]4[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=4[O:27][CH2:28][C:22]=3[CH:21]=2)[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 158072-EthylbenzimidazoleHCID 67211222HCID 67211222, compound

Product 1

HCID 67211040HCID 67211040, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 1] 2-Ethylbenzimidazole (163 mg, 1.12 mmol) was dissolved in DMF (5.0 mL), potassium carbonate (0.700 g, 5.07 mmol) was added, and the mixture was stirred for 15 min. To this mixture was added (E)-2-(8-chloromethyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene)propiononitrile (300 mg, 1.01 mmol) obtained in Reference Example B5, and the mixture was stirred at 60° C. for 3 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/5) to give (E)-2-[8-(2-ethylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (318 mg, 70%).

Workup

  1. customobtained in Reference Example B5
  2. stirringthe mixture was stirred at 60° C. for 3 hr
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1 to 5/5)

Sources & evidence

ORD record
ord-24ae56f771934d7ba975561223960f75
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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