Ammonium Chloride → HCID 22736667, compound

HRID 50924

Reaction equation

HRID 50924 reaction equation
[Cl-].[NH4+].[N+:3]([C:6]1[CH:28]=[CH:27][C:9]2[N:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:11](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][C:8]=2[CH:7]=1)([O-])=O>C(O)C.O.[Fe]>[NH2:3][C:6]1[CH:28]=[CH:27][C:9]2[N:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:11](/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][C:8]=2[CH:7]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 22736675(E)-5-Nitro-1-(2-pyridyl)-2-styryl-1H-benzimidazole

Product 1

HCID 22736667HCID 22736667, compoundYield 70.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (1.95 g, 35 mmol) and ammonium chloride (200 mg, 3.7 mmol) was added to a solution of (E)-5-nitro-1-(2-pyridyl)-2-styryl-1H-benzimidazole (2.41 g, 7.0 mmol) in ethanol (50 ml) and water (25 ml). After the reaction mixture was refluxed for 3 h, the hot reaction mixture was filtered through a pad of celite and the filtrate was evaporated under reduced pressure. The obtained residue was partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (200 ml). The combined extracts were washed with brine (20 ml), dried (sodium sulfate) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 200 g; n-hexane/ethyl acetate (1/2)) and obtained solids (1.54 g, 70%) were recrystallized from ethyl acetate to afford the titled compound as brown solids. MW: 312.38; mp: 146.0-148.0° C.; 1H-NMR (CDCl3) δ: 8.75 (1H. ddd, J=4.8, 1.8, 1.1 Hz), 8.01-7.91 (1H, m), 7.95 (1H, d, J=16.0 Hz), 7.56-7.23 (8H, m), 7.13 (1H, d, J=16.0 Hz), 7.11 (1H, d, J=2.2 Hz), 6.69 (1H, dd, J=8.8, 2.2 Hz), 3.70 (2H, br.s).

Workup

  1. temperatureAfter the reaction mixture was refluxed for 3 h
  2. filtrationthe hot reaction mixture was filtered through a pad of celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe obtained residue was partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate solution (200 ml)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with ethyl acetate (200 ml)
  7. washThe combined extracts were washed with brine (20 ml)
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (silica gel, 200 g; n-hexane/ethyl acetate (1/2))

Sources & evidence

ORD record
ord-5c47c4885f094fe2999164ff53f9a869
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

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