Dimethylformamide → 5-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole

HRID 2375278Notes

Reaction equation

HRID 2375278 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7](=[O:9])[CH3:8])[N:6]=1.C[C:11]([N:13]([CH3:15])[CH3:14])=O.[CH3:16]N(C=O)C>>[CH3:11][N:13]([CH3:15])[CH:14]=[CH:8][C:7]([C:5]1[N:6]([CH3:16])[C:2]([CH3:1])=[N:3][CH:4]=1)=[O:9]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 31374DimethylacetamideHCID 178467223HCID 178467223, compound

Product 1

HCID 693105495-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazoleYield 57%

Procedure

2-Methyl-4-acetylimidazole (Tetrahedron letters 1985, 26 (29), 3423-3426; 129 g, 1.04 mol) was dissolved in a mixture of DMF (900 ml) and DMF.DMA (1.51) and the mixture heated under reflux, under an atmosphere of nitrogen, for 18 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 (115 g, 57%) as a pale brown crystalline solid. NMR: 2.13 (s, 3H), 2.95 (s, 6H), 3.78 (s, 3H), 5.56 (d, 1H), 7.50 (d, 1H), 7.53 (s, 1H); m/z 194.

Workup

  1. temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
  2. customcrystallised
  3. filtrationThe solid product was collected by filtration
  4. washwashed with DMF
  5. dry with materialDMA and then ether and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-c93e424ac56f4f20933226add52e787d
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

Loading…