O-Phenylenediamine → 4-(1h-Benzimidazol-2-yl)benzoic acid

HRID 1068547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068547
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].C(C(C#N)=C(C#N)C#N)#N>CC(N(C)C)=O>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]2[NH:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:19]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2]

Komponenten

5

Edukt 3

HCID 7243O-PhenylenediamineHCID 120884-Formylbenzoic acidHCID 12635Tetracyanoethylene

Produkt 1

HCID 7594194-(1h-Benzimidazol-2-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Resin-bound 4-carboxybenzaldehyde (subn. 0.65 mmol/g, 400 mg, 0.26 mmol) was suspended in DMA (3 mL) and treated with 1,2-phenylenediamine (2.6 mmol) and TCNE (2.6 mmol). The suspension was sonicated for 1 h and shaken at 25° C. for an additional 22 h. The resin was filtered, washed with DMA, DCM, and dried under high vacuum. The benzimidazole was cleaved from the solid support with 20% (v/v) TFA in DCM (2×5 mL, 15 min) and the combined filtrates were evaporated to give the title compound. 1H NMR (d6-DMSO) δ 7.35-7.43 (m, 2H), 7.69-7.78 (m, 2H), 8.19 (d, 2H, J=8.3 Hz), 8.26-8.34 (m, 2H), 12.50-14.20 (br s, CO2H). MS (API-ES+) m/z 239 (M+H).

Aufarbeitung

  1. customThe suspension was sonicated for 1 h
  2. filtrationThe resin was filtered
  3. washwashed with DMA, DCM
  4. customdried under high vacuum
  5. customwas cleaved from the solid support with 20% (v/v) TFA in DCM (2×5 mL, 15 min)
  6. customthe combined filtrates were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1482ec34c37b4b23ad9bfad48390d069
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06251689B1

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