Imidazole → (1H-Imidazol-1-yl)(2,4,6-trimethylphenyl)methanone

HRID 638007Notes

Reaction equation

HRID 638007 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:8]=1[C:9](Cl)=[O:10]>CCOCC>[CH3:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:8]=1[C:9]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:10]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 970382,4,6-Trimethylbenzoyl chloride

Product 1

HCID 12852198(1H-Imidazol-1-yl)(2,4,6-trimethylphenyl)methanoneYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

136 g (2.0 moles) of imidazole in 1,000 ml of ether are initially taken, and 146 g (0.8 mole) of 2,4,6-trimethylbenzoyl chloride are added dropwise to the stirred mixture in the course of 30 minutes at from 10° to 20° C. Stirring is continued for 5 hours at room temperature, and the precipitated imidazole hydrochloride is filtered off under suction, the filtrate is evaporated down and the residue is distilled to give 116.4 g (68% of theory) of N-(2,4,6-trimethylbenzoyl)-imidazole of boiling point 128° C./0.01 mbar.

Workup

  1. filtrationthe precipitated imidazole hydrochloride is filtered off under suction
  2. customthe filtrate is evaporated down
  3. distillationthe residue is distilled

Sources & evidence

ORD record
ord-cb6db476f1d64cf1bb74236ed09f6f3a
Source dataset
uspto-grants-1985_12
Patent number
US04559398

Reaction notes

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