3,4,6-Trifluorobenzene-1,2-diamine → HCID 18537794, Verbindung

HRID 412728

Reaktionsgleichung

Reaktionsgleichung von HRID 412728
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[NH2:11].C(O[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=N)C>C(O)C>[F:8][C:7]1[C:2]2[N:1]=[C:15]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:11][C:3]=2[C:4]([F:10])=[C:5]([F:9])[CH:6]=1

Komponenten

4

Edukt 2

HCID 5956243,4,6-Trifluorobenzene-1,2-diamineHCID 13451607HCID 13451607, Verbindung

Produkt 1

HCID 18537794HCID 18537794, VerbindungAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1,2-diamino-3,4,6-trifluorobenzene (1.92 g, 11.8 mmol), ethyl 2-ethoxycarbonimidoylpropionate (3.1 g, 14.7 mmol) and absolute ethanol (6 ml) was heated at reflux until no further progression of the reaction was indicated by TLC indicated the reaction was not progressing further, filtered from NH4Cl and concentrated. The residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1) to give ethyl 2-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)propionate (1.37 g, 42%) as a tan crystalline solid; NMR (CDCl3): δ 10.35 (s, ½H), δ 7.05 (s, ½H), 6.7 (m, 1H), δ 4.25 (dd, 2H), δ 4.15 (dd, 1H), δ 1.73 (d, 3H), δ 1.31 (t, 3H); M+ 272.9 (calcd for C12H11F3N2O2: 272.23).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux until no further progression of the reaction
  3. filtrationfiltered from NH4Cl
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica (hexane: methylene chloride: ethyl acetate, 5:5:1)

Quellen und Nachweise

ORD-Eintrag
ord-cbd479142c1c47c890fa64a146dcdc43
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562854B2

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