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

HRID 1582303노트

반응식

HRID 1582303 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 23925Iron촉매

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-6c99b966daca4caab73e3eed285b4192
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734191B2

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