Acetic Acid → Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoate

HRID 1582303ノート

反応式

HRID 1582303 の反応式
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=O)=[CH:6][C:5]=1C1C=CC=CC=1[N+]([O-])=O.[C:23](O)(=O)[CH3:24]>[Fe]>[N:10]1[C:8]2[CH:7]=[CH:6][CH:5]=[CH:23][C:24]=2[NH:10][C:8]=1[C:7]1[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:22])=[CH:12][CH:11]=1

参加物

4

反応物 2

HCID 176Acetic AcidHCID 68619015(2-Nitrophenyl)-terephthalamic acid methyl ester

生成物 1

HCID 2328806Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoate収率 86%

試薬・触媒・溶媒 1

HCID 23925Iron触媒

実験手順

To a solution of (2-nitrophenyl)-terephthalamic acid methyl ester (0.23 g, 0.76 mmol) in glacial acetic acid (2.5 mL) was added iron powder (<5 μm mesh, 0.12 g, 2.1 mmol) and the mixture stirred at reflux for 1 h. The mixture was cooled, stirred at room temperature for 2 h and concentrated under reduced pressure. The residue was partitioned between saturated sodium bicarbonate (10 mL) and ethyl acetate (10 mL), the phases separated and the organic layer washed with saturated NaHCO3 (10 mL). The organic extract was dried (MgSO4), filtered and concentrated to give cyclized methyl 4-(benzimidazol-2-yl)-benzoate (0.163 g, 86%). 1H NMR (CDCl3) δ3.96 (s, 3H), 7.32 (m, 2H), 7.53 (br, 1H), 7.84 (br, 1H), 8.17 (m, 4H), 9.65 (br, 1H (NR)).

後処理

  1. temperatureat reflux for 1 h
  2. temperatureThe mixture was cooled
  3. stirringstirred at room temperature for 2 h
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between saturated sodium bicarbonate (10 mL) and ethyl acetate (10 mL)
  6. customthe phases separated
  7. washthe organic layer washed with saturated NaHCO3 (10 mL)
  8. extractionThe organic extract
  9. dry with materialwas dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-6c99b966daca4caab73e3eed285b4192
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

反応ノート

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