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

HRID 2410116Notes

Reaction equation

HRID 2410116 reaction equation
[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]

Participants

3

Reactant 2

HCID 75645CyclobutylamineHCID 10975874HCID 10975874, compound

Product 1

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

Conditions

Temperature
70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b720a9a4128b4cf096242440c56978d8
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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