Cinnamoyl Chloride → (E)-1-(3-Pyridyl)-2-styryl-1H-benzimidazole

HRID 382511

Reaction equation

HRID 382511 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:2]=1.[C:15](Cl)(=O)/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]2/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 5354261Cinnamoyl ChlorideHCID 22736684N-(3-pyridyl)-o-phenylenediamine

Product 1

HCID 22736740(E)-1-(3-Pyridyl)-2-styryl-1H-benzimidazoleYield 34%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred suspension of N-(3-pyridyl)-o-phenylenediamine (0.93 g, 5 mmol; Kirsch, P.; Schoenleben-Janas, A.; Schirmer, R. H. Liebigs Ann. Org. Bioorg. Chem., 1995, 7, 1275) in xylene (60 ml) was added (E)-cinnamoyl chloride (0.83 g, 5 mmol). After stirring at the room temperature for 1 h, the resulting mixture was heated to reflux removing water using a Dean-Stark apparatus for 11 h. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved into ethyl acetate (100 ml), washed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml), dried (magnesium sulfate) and concentrated to dryness. The residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1)) to give 0.77 g (34%) of brown solids. Recrystallization from isopropyl ether yielded 0.50 g of the titled compound as pink solids.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux
  3. customremoving water using a Dean-Stark apparatus for 11 h
  4. temperatureAfter cooling
  5. concentrationthe reaction mixture was concentrated to dryness
  6. dissolutionThe residue was dissolved into ethyl acetate (100 ml)
  7. washwashed consecutively with saturated aqueous sodium bicarbonate solution (50 ml) and brine (50 ml)
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by column chromatography (silica gel, 165 g; n-hexane/ethyl acetate (3/2 to 1/1))

Sources & evidence

ORD record
ord-df1a59ec226b4855a5da2a2d9bf44d63
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Linked notes

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