Formic Acid → 7-Chloro-1H-benzo[d]imidazol-5-amine

HRID 429580

Reaktionsgleichung

Reaktionsgleichung von HRID 429580
ClC1C(N)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1.C(O)=O.[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH:28]C=O)[CH:20]=1.C(N)=O>C(OC(=O)C)(=O)C.Cl.[Pd].CCO>[Cl:18][C:19]1[C:27]2[NH:26][CH:25]=[N:24][C:23]=2[CH:22]=[C:21]([NH2:28])[CH:20]=1

Komponenten

9

Edukt 4

HCID 284Formic AcidHCID 713FormamideHCID 190526-Chloro-2,4-dinitroanilineHCID 178522168HCID 178522168, Verbindung

Produkt 1

HCID 1785076737-Chloro-1H-benzo[d]imidazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Methanolic solution of 6-chloro-2,4-dinitroaniline (2.4 g, 11 mmol) was stirred overnight with 100 mg of 10% Pd/C under H2. Reaction mixture was filtered and concentrated in vacuo to provide an oil which was dissolved in 10 ml of acetic anhydride and 10 ml of formic acid and stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding a brown oil which was characterized as 4-chloro-6-foramidylbenzimidazole in NMR analysis. The formamide was dissolved in 20 ml of HCl sat'd EtOH and stirred for 3h at 25° C. The reaction mixture was purified in column chromatography (5% MeOH/EtOAc) to provide 0.89 g (5.3 mmol, 48% overall) of the desired product.

Aufarbeitung

  1. customReaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated in vacuo
  4. customto provide an oil which
  5. temperatureat reflux for 12 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customyielding a brown oil which
  8. customThe reaction mixture was purified in column chromatography (5% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-98b5b6c4ca6e4c908c7280faa5b61774
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316637B1

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