Cyclopropylamine → ethyl 1-cyclopropyl-1H-imidazole-4-carboxylate

HRID 2410117Notes

Reaction equation

HRID 2410117 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)C[CH2:14]1>>[CH2:1]([O:3][C:4]([C:5]1[N:10]=[CH:11][N:7]([CH:9]2[CH2:14][CH2:13]2)[CH:6]=1)=[O:12])[CH3:2]

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 10975874HCID 10975874, compound

Product 1

HCID 57680715ethyl 1-cyclopropyl-1H-imidazole-4-carboxylate

Conditions

Temperature
75 °C

Procedure

The stirred mixture of (Z)-3-dimethylamino-2-isocyano-acrylic acid ethyl ester (17.0 g, 100 mmol) and cyclopropylamine (17.21 g, 300 mmol) was heated for 5 h at 75° C. The reaction mixture was cooled to rt and concentrated. Purification of the residue by flash chromatography (EtOAc/hexane, 5:1) gave the title compound as an orange oil. tR: 0.61 min (LC-MS 2); ESI-MS: 181.2 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.85 (s, 1H), 7.79 (s, 1H), 4.18 (q, 2H), 3.55 (m, 1H), 1.23 (t, 3H), 0.91-1.02 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-a3d37d04bae94fe4bccb1b2b09b6fe95
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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