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

HRID 1064327Notes

Reaction equation

HRID 1064327 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 (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 DMFDMA 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 DMFDMA
  5. dry with materialether and dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-517416de2f1a41289b675a4c6bd7bd39
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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