Cyclobutylamine → 1-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410116
[CH2:1]([O:3][C:4](=[O:12])/[C:5](/[N+:10]#[C-:11])=[CH:6]/[N:7]([CH3:9])C)[CH3:2].[CH:13]1(N)[CH2:16]C[CH2:14]1>>[CH2:1]([O:3][C:4]([C:5]1[N:10]=[CH:11][N:7]([CH:9]2[CH2:16][CH2:13][CH2:14]2)[CH:6]=1)=[O:12])[CH3:2]

Komponenten

3

Edukt 2

HCID 75645CyclobutylamineHCID 10975874HCID 10975874, Verbindung

Produkt 1

HCID 866721321-cyclobutyl-1H-imidazole-4-carboxylic acid ethyl ester

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The stirred mixture of (Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester (17.0 g, 100 mmol) and cyclobutaneamine (21.79 g, 300 mmol) was heated for 2.5 h at 70° C. The reaction mixture was cooled to rt and concentrated. The residue was purified by flash chromatography (EtOAc/hexane, 5:1) to afford the title compound as an orange oil. tR: 0.70 min (LC-MS 2); ESI-MS: 195.2 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 8.03 (s, 1H), 7.83 (s, 1H), 4.73 (m, 1H), 4.18 (q, 2H), 2.36 (m, 4H), 1.74 (m, 2H), 1.24 (t, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (EtOAc/hexane, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-b720a9a4128b4cf096242440c56978d8
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815926B2

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