Triethylamine → 2-Phenyl-1-(2,4,6-trimethylbenzoyl)-1H-imidazole

HRID 1380146Notes

Reaction equation

HRID 1380146 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:19][C:20]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:21]=1[C:22](Cl)=[O:23].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:19][C:20]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:21]=1[C:22]([N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 695912-PhenylimidazoleHCID 970382,4,6-Trimethylbenzoyl chloride

Product 1

HCID 30230442-Phenyl-1-(2,4,6-trimethylbenzoyl)-1H-imidazoleYield 78.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

144.2 g (1.00 mole) of 2-phenylimidazole are dissolved at 90° C. in 900 ml of toluene. 104.2 g (1.03 moles) of triethylamine are added to this solution, and a solution of 182.6 g (1.00 mole) of 2,4,6-trimethylbenzoyl chloride in 300 ml of toluene is added dropwise at 90° C. in the course of 2 hours, triethylamine hydrochloride being precipitated. The latter is filtered off with suction at room temperature and extracted by washing with toluene. Concentrating the filtrate gives 296 g of crude product, recrystallisation of which from 580 ml of acetonitrile gives a total of 227.3 g of 1-(2,4,6-trimethylbenzoyl)-2-phenylimidazole (78.3% of theory).

Workup

  1. customprecipitated
  2. filtrationThe latter is filtered off with suction at room temperature
  3. extractionextracted
  4. washby washing with toluene
  5. concentrationConcentrating the filtrate
  6. customgives
  7. custom296 g of crude product, recrystallisation of which from 580 ml of acetonitrile

Sources & evidence

ORD record
ord-055f068c72994a5784778f01c32dd378
Source dataset
uspto-grants-1986_04
Patent number
US04579916

Reaction notes

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