Benzene → Ethyl 5-methyl-2-phenylimidazole-4-acetate

HRID 1580096Notes

Reaction equation

HRID 1580096 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([OH:16])=[O:15].[CH2:17](O)[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 241BenzeneHCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 215650655-Methyl-2-phenylimidazole-4-acetic acid

Product 1

HCID 22597552Ethyl 5-methyl-2-phenylimidazole-4-acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

About 40 g of 5-methyl-2-phenylimidazole-4-acetic acid, 100 ml of absolute ethanol, 1 g of p-toluenesulfonic acid and 650 ml of benzene is heated under reflux with azeotropic removal of water overnight (about 15 hours). The reaction mixture is filtered, washed with sodium bicarbonate solution, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo to yield the product, ethyl 5-methyl-2-phenylimidazole-4-acetate.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-704dcf766cc24e3e82f991e7e055e8d0
Source dataset
uspto-grants-1976_01
Patent number
US03932445

Reaction notes

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