Reaction #1810841

Reaction equation

1-Cyclobutyl-2-methyl-4-acetylimidazole

DMF

DMA

→

title compound

Yield 47.0%

5-(3-Dimethylaminoprop-2-enoyl)-1-cyclobutyl-2-methylimidazole

Yield 47.0%

Conditions

Workup

1. 1
   Temperatureat reflux, under an atmosphere of nitrogen, for 54 hours
2. 2
   Othercrystallised
3. 3
   FiltrationThe solid product was collected by filtration
4. 4
   Washwashed with DMF
5. 5
   DryingDMA and then ether and dried under vacuum at 40° C.

Procedure

1-Cyclobutyl-2-methyl-4-acetylimidazole (Method 3; 2.52 g, 14.1 mmol) was dissolved in DMF.DMA (75 mL) and the mixture heated at reflux, under an atmosphere of nitrogen, for 54 hours. The reaction mixture was allowed to cool to ambient temperature the product crystallised. The solid product was collected by filtration, washed with DMF.DMA and then ether and dried under vacuum at 40° C. to give the title compound (1.55 g, 47%) as a pale brown crystalline solid. NMR: 1.72 (m, 2H), 2.28 (m, 2H), 2.39 (s, 3H), 2.64 (m, 2H), 2.95 (m, 6H), 5.22 (m, 1H), 5.50 (d, 1H), 7.39 (s, 1H), 7.51 (d, 1H).

Source