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

HRID 2410116ノート

反応式

HRID 2410116 の反応式
[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]

参加物

3

反応物 2

HCID 75645CyclobutylamineHCID 10975874HCID 10975874、化合物

生成物 1

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

反応条件

温度
70 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b720a9a4128b4cf096242440c56978d8
出典データセット
uspto-grants-2014_08
特許番号
US08815926B2

反応ノート

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