Imidazole → Acetophenone, 2-(1-imidazolyl)-2',3',5',6'-tetramethyl-

HRID 1680650Notes

Reaction equation

HRID 1680650 reaction equation
Br[CH2:2][C:3]([C:5]1[C:11]([CH3:12])=[C:10]([CH3:13])[CH:9]=[C:7]([CH3:8])[C:6]=1[CH3:14])=[O:4].CN(C)C=O.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>O>[N:20]1([CH2:2][C:3]([C:5]2[C:11]([CH3:12])=[C:10]([CH3:13])[CH:9]=[C:7]([CH3:8])[C:6]=2[CH3:14])=[O:4])[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6228DimethylformamideHCID 2648242-bromo-1-(2,3,5,6-tetramethylphenyl)ethanone

Product 1

HCID 52759Acetophenone, 2-(1-imidazolyl)-2',3',5',6'-tetramethyl-Yield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture containing 2.55 g of 3-bromoacetyl-durene, prepared as described in Example 4, 3 ml of dimethylformamide and 3.40 g of imidazole, was stirred for 8 hours at 80° C. At the end of the reaction, the mixture was cooled to room temperature and 25 ml of water were added. The precipitate thus obtained was filtered off, dried and crystallized from benzene to give 1.5 g of the title compound. M.P. 176°-8° C., yield 62%.

Workup

  1. customprepared
  2. customAt the end of the reaction
  3. temperaturethe mixture was cooled to room temperature
  4. customThe precipitate thus obtained
  5. filtrationwas filtered off
  6. customdried
  7. customcrystallized from benzene

Sources & evidence

ORD record
ord-432d2bfa73a04984a77de39e461e182b
Source dataset
uspto-grants-1981_06
Patent number
US04275071

Reaction notes

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