N-bromobutanimide → 5-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine

HRID 1797113

Reaction equation

HRID 1797113 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[N:11][N:10]=[C:9]1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:17][CH:18]=1.C1C(=O)N([Br:32])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Br:32][C:12]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[C:9]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][CH:18]=2)=[N:10][N:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 220192605-[4-(2-Bromophenyl)-4h-1,2,4-triazol-3-yl]-2-phenylpyridine

Product 1

HCID 220192295-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridineYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

5-[4-(2-Bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine prepared in the Production Example 2 was dissolved in a mixture solvent of carbon tetrachloride (100 ml) and acetic acid (100 ml), followed by addition of n-bromosuccinimide (5.90 g), and refluxed under heating for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue, and extracted with chloroform. Subsequently, the organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1), to afford the entitled compound as yellow solid (6.96 g, 69%). The physico-chemical values are as follows.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 3 hours
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionSaturated aqueous sodium hydrogen carbonate solution was added to the resulting residue
  5. extractionextracted with chloroform
  6. dry with materialSubsequently, the organic layer was dried over anhydrous magnesium sulfate
  7. customAfter the solvent was evaporated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-fdc856b9af5849d68a71d6ba1cb939de
Source dataset
uspto-grants-2006_04
Patent number
US07034047B2

Linked notes

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