Imidazole → 2-[(4-Bromophenyl)methyl]-1-(1H-imidazol-1-yl)-3,3-dimethylbutan-1-one

HRID 2412565Notes

Reaction equation

HRID 2412565 reaction equation
C(#N)C.[NH:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C(N(CC)CC)C.[Br:16][C:17]1[CH:31]=[CH:30][C:20]([CH2:21][CH:22]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23](Cl)=[O:24])=[CH:19][CH:18]=1>O>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]([C:26]([CH3:27])([CH3:29])[CH3:28])[C:23]([N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[O:24])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6342AcetonitrileHCID 8471TriethylamineHCID 13563057HCID 13563057, compound

Product 1

HCID 1842472-[(4-Bromophenyl)methyl]-1-(1H-imidazol-1-yl)-3,3-dimethylbutan-1-oneYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of acetonitrile were added 0.75 g of imidazole and 1.2 g of triethylamine, and 3.0 g of α-(p-bromobenzyl)-tert-butyl-acetic acid chloride was then added dropwise at room temperature. Thereafter, the mixture was stirred at room temperature for 6 hours, poured into 300 ml of water and extracted with 300 ml of chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily product obtained was recrystallized from diisopropyl ether to obtain 2.39 g of N-[α-(p-bromobenzyl)-tert-butylacetyl]imidazole (compound No. 4). m.p. 101°-102° C.

Workup

  1. additionwas then added dropwise at room temperature
  2. extractionextracted with 300 ml of chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe oily product obtained
  6. customwas recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-0a3e140f273d4fd693acab2cbdb46245
Source dataset
uspto-grants-1985_01
Patent number
US04493842

Reaction notes

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