Acetonitrile → Ethyl 5-methyl-2-(4-methylphenyl)-1H-imidazole-4-carboxylate

HRID 1252374Notes

Reaction equation

HRID 1252374 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.O=[C:11]([C:17](=O)[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(#[N:22])C>>[CH3:18][C:17]1[NH:22][C:6]([C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=2)=[N:7][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 660354-MethylbenzylamineHCID 12260829Ethyl 2,3-dioxobutanoate

Product 1

HCID 43445104Ethyl 5-methyl-2-(4-methylphenyl)-1H-imidazole-4-carboxylate

Procedure

A mixture of 10.7 g of 4-methylbenzylamine, 12.7 g of 2,3-dioxobutyric acid, ethyl ester, (Z)-2-oxime and 160 ml of acetonitrile was stirred and refluxed for 3.5 hours. The mixture was cooled, the solid collected and recrystallized from ethanol, giving 6.2 g of 5-methyl-2-(4-methylphenyl)-1H-imidazole-4-carboxylic acid, ethyl ester.

Workup

  1. temperaturerefluxed for 3.5 hours
  2. temperatureThe mixture was cooled
  3. customthe solid collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-24b851c410a74f65b7243447edd514f9
Source dataset
uspto-grants-1988_05
Patent number
US04743586

Reaction notes

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