Imidazole → HCID 69257272, compound

HRID 2038338Notes

Reaction equation

HRID 2038338 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:6]([O:8]C(OCC)C1C=CC=CC=1)[CH3:7].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:6]([O:8][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:29][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:7]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 69884(Diethoxymethyl)benzene

Product 1

HCID 69257272HCID 69257272, compound

Conditions

Temperature
110 °C

Procedure

A mixture of imidazole (1.0 g, 14.7 mmol), benzaldehyde diethylacetal (58.8 mmol), and p-toluenesulfonic acid (84 mg, 0.441 mmol) was heated neat at 110° C. for 1-3 days, accompanied by concurrent distillation of ethanol. After cooling, sodium carbonate (0.47 g, 4.41 mmol) was added and the crude mixture was distilled under vacuum (150-170° C./0.5 mmHg) to give N-ethoxybenzylimidazole derivatives (1-8) (15-75% yield).

Workup

  1. distillationaccompanied by concurrent distillation of ethanol
  2. temperatureAfter cooling
  3. distillationthe crude mixture was distilled under vacuum (150-170° C./0.5 mmHg)

Sources & evidence

ORD record
ord-33684b2a3ff84a0cab342e7cd7854d0d
Source dataset
uspto-grants-2013_11
Patent number
US08575359B2

Reaction notes

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