Dimethylformamide → HCID 67037586, compound

Reaction equation

[CH:1]1([N:5]2[CH:9]=[C:8](C(=O)C)[N:7]=[C:6]2[CH3:13])[CH2:4][CH2:3][CH2:2]1.[CH3:14][C:15]([N:17]([CH3:19])[CH3:18])=O.CN([CH:23]=[O:24])C>>[CH3:18][N:17]([CH3:19])[CH:15]=[CH:14][C:23]([C:9]1[N:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[C:6]([CH3:13])=[N:7][CH:8]=1)=[O:24]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 31374Dimethylacetamide

HCID 688810941-Cyclobutyl-2-methyl-4-acetylimidazole

Product 1

HCID 67037586HCID 67037586, compoundYield 47%

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).