Ammonia → HCID 19864533, compound
Reaction equation
[C:1]([NH:5][C:6](=[O:11])[CH2:7][C:8](=O)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[NH3:12]>>[C:1]([NH:5][C:6](=[O:11])/[CH:7]=[C:8](\[NH2:12])/[CH3:9])([CH3:4])([CH3:3])[CH3:2]Participants
3
Procedure
N-t-butyl-3-ketobutanamide (0.29 g) was dissolved in saturated ethanolic ammonia (15 ml) and stirred overnight at room temperature. The solution was evaporated to yield N-t-butyl-3-aminocrotonamide which was used directly. The crude residue was dissolved in ethanol (8 ml), 2-chlorobenzaldehyde (0.28 g) and ethyl 4-[2-(2-methylbenzimidazol-1-yl)ethoxy]-3-ketobutanoate (0.61 g) were added. The mixture was heated at reflux overnight, cooled and the solvent removed under reduced pressure. The residue was chromatographed on silica eluting with 4% diethylamine in ethyl acetate. The fractions containing the product were combined and evaporated. The residue was re-chromatographed on silica eluting with 5% methanol in ethyl acetate. The fractions containing the product were combined and evaporated to yield the title compound (0.17 g, 15%). m.p. 157°-161° C. Found: C, 65.66; H, 6.68; N, 9.74. C31H37C1N4O4 requires C, 65.89; H, 6.60; N, 9.91%.