6-Nitro-2-(trifluoromethyl)-1H-benzimidazole → 5-Amino-2-(trifluoromethyl)benzimidazole

HRID 2299149

Reaktionsgleichung

Reaktionsgleichung von HRID 2299149
[N+](C1C=CC(N)=C(N)C=1)([O-])=O.[F:12][C:13]([F:27])([F:26])[C:14]1[NH:15][C:16]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:17]=2[N:18]=1.[N+](C1NC2C=CC=CC=2N=1)([O-])=O>FC(F)(F)C(O)=O.CCOC(C)=O.CO.[Pd]>[F:27][C:13]([F:12])([F:26])[C:14]1[NH:15][C:16]2[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:17]=2[N:18]=1

Komponenten

8

Edukt 3

HCID 675956-Nitro-2-(trifluoromethyl)-1H-benzimidazoleHCID 972342-Nitro-1H-benzimidazoleHCID 51117914-Nitro-1,2-phenylenediamine

Produkt 1

HCID 193455-Amino-2-(trifluoromethyl)benzimidazoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-nitro-1,2-phenylenediamine (3.0 g, 20 mmol) in 15 ml of trifluoroacetic acid was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo to yield a oily residue, which was dissolved in 100 ml of EtOAc and washed with aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo to provide an oil which was characterized as 2-trifluoromethyl-5-nitrobenzimidazole and subjected to the following reaction without further purification. The nitrobenzimidazole and 500 mg of 10% Pd-C were dissolved in 100 ml of MeOH and stirred for 12 h under H2. The reaction mixture was filtered and concentrated in vacuo, yielding 3.2 g (16 mmol, 80%) of the desired product.

Aufarbeitung

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield a oily residue, which
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto provide an oil which
  8. customsubjected to the following reaction without further purification
  9. filtrationThe reaction mixture was filtered
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab4002b281cb41b58dbf56acf2212ce5
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495583B1

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