Dimethylacetamide → HCID 69205290, compound

HRID 268586Notes

Reaction equation

HRID 268586 reaction equation
[C:1]([C:4]1[N:8]([CH:9]([CH3:11])[CH3:10])[C:7]([CH3:12])=[N:6][C:5]=1[CH3:13])(=[O:3])[CH3:2].C[C:15]([N:17]([CH3:19])[CH3:18])=O>CN(C=O)C>[CH3:15][N:17]([CH3:19])[CH:18]=[CH:2][C:1]([C:4]1[N:8]([CH:9]([CH3:11])[CH3:10])[C:7]([CH3:12])=[N:6][C:5]=1[CH3:13])=[O:3]

Participants

4

Reactant 2

HCID 31374DimethylacetamideHCID 69205360HCID 69205360, compound

Product 1

HCID 69205290HCID 69205290, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

Workup

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

Sources & evidence

ORD record
ord-9f64c0c2bb9e49708480a838f8468cf6
Source dataset
uspto-grants-2008_11
Patent number
US07446105B2

Reaction notes

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