Ethyl Acetate → HCID 67210477, compound

HRID 452138Notes

Reaction equation

HRID 452138 reaction equation
[CH2:1]([C:3]1[NH:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]1[CH:40]=[CH:39][C:25]2/[C:26](=[C:35](/[CH3:38])\[C:36]#[N:37])/[C:27]3[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=3[O:29][CH2:30][C:24]=2[CH:23]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([C:3]1[N:4]([CH2:21][C:22]2[CH:40]=[CH:39][C:25]3/[C:26](=[C:35](/[CH3:38])\[C:36]#[N:37])/[C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[O:29][CH2:30][C:24]=3[CH:23]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67211222HCID 67211222, compoundHCID 178437563HCID 178437563, compound

Product 1

HCID 67210477HCID 67210477, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[step 1] 2-Ethyl-4-phenylimidazole (Tetrahedron Lett. 2001, p 7079; 192 mg, 1.12 mmol) was dissolved in DMF (4.8 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 6/4) to give (E)-2-[8-(2-ethyl-4-phenylimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]propiononitrile (434 mg, 99%).

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 6/4)

Sources & evidence

ORD record
ord-d5b89c9b5bb346c08cad1be3b43e29a7
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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