Reaction #355768

Reaction equation

5-Acetyl-1-isopropyl-2,4-dimethylimidazole

DMA

→

title compound

Yield 13.0%

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-isopropyl-2,4-dimethylimidazole

Yield 13.0%

Solvents

DMF

Conditions

Workup

1. 1
   Temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
2. 2
   OtherThe volatiles were evaporated in vacuo
3. 3
   OtherThe residue was purified by flash silica chromatography DCM

Procedure

5-Acetyl-1-isopropyl-2,4-dimethylimidazole (Method 8; 3g, 16.5 mmol) was dissolved in a mixture DMF.DMA (100 ml) and the mixture heated under reflux, under an atmosphere of nitrogen, for 18 hours. The volatiles were evaporated in vacuo. The residue was purified by flash silica chromatography DCM:MeOH (increasing in polarity from 100:0 to 95:5) to give the title compound (510 mg, 13%) as an orange oil. NMR 1.38 (d, 6H), 2.18 (s, 3H), 2.30 (s, 3H), 2.83 (s, 3H), 3.08 (s, 3H), 4.72 (q, 1H), 5.21 (d, 1H), 7.46 (d, 1H); m/z 236

Source