Ammonium Chloride → HCID 22736667、化合物

HRID 50924

反応式

HRID 50924 の反応式
[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

参加物

6

反応物 2

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

生成物 1

HCID 22736667HCID 22736667、化合物収率 70.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-5c47c4885f094fe2999164ff53f9a869
出典データセット
uspto-grants-2004_03
特許番号
US06713482B2

関連ノート

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