HCID 69312069, compound → HCID 67037521, compound

HRID 2117754Notes

Reaction equation

HRID 2117754 reaction equation
[CH:1]([N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][N:6]=[C:5]1[CH2:12][O:13][CH3:14])([CH3:3])[CH3:2]>CN(C=O)C>[CH3:1][N:4]([CH3:8])[CH:5]=[CH:10][C:9]([C:8]1[N:4]([CH:1]([CH3:3])[CH3:2])[C:5]([CH2:12][O:13][CH3:14])=[N:6][CH:7]=1)=[O:11]

Participants

3

Reactant 1

HCID 69312069HCID 69312069, compound

Product 1

HCID 67037521HCID 67037521, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Isopropyl-2-methoxymethyl-5-acetylimidazole (Method 12; 3.34 g, 17 mmol) was dissolved in a mixture of DMF (34 ml) and DMF.DEA (11.5 ml, 68 mmol) and the mixture heated under reflux, under an atmosphere of nitrogen, for 18 hours. The volatiles were removed by evaporation. A solid was precipitated with ether, collected by filtration and air dried to yield the title compound as a brown solid (2.25 g, 53%); NMR 1.43 (d, 6H), 2.95 (m, 6H), 3.20 (s, 3H), 4.46 (s, 2H), 5.00 (m, 1H), 5.56 (d, 1H), 7.55 (m, 2H); m/z 252.

Workup

  1. temperatureDEA (11.5 ml, 68 mmol) and the mixture heated
  2. temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
  3. customThe volatiles were removed by evaporation
  4. customA solid was precipitated with ether
  5. filtrationcollected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-18bb4370ff2844f8a7c17b36ae71429d
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

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