Imidazole → (3-Bromophenyl)-1H-imidazol-2-ylmethanone

HRID 272654Notes

Reaction equation

HRID 272654 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](Cl)=[O:18].[OH-].[Na+]>N1C=CC=CC=1.O>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 3418429(3-Bromophenyl)-1H-imidazol-2-ylmethanoneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of imidazole (2.66 g, 39.1 mmol) and triethylamine (Et3N) 8.03 g, 79.4 mmol) in pyridine at 0° C. is treated with 3-bromobenzoyl chloride (17.5 g, 79.9 mmol), stirred for 5 min, allowed to warm to room temperature for 45 min, treated with an aqueous sodium hydroxide solution (7.5 N, 20 mL, 150 mmol), heated at reflux temperature for 2 h, cooled to room temperature, diluted with water, further cooled with an ice bath for 1 h and filtered. The filtercake is washed with water and dried under vacuum at 50° C. overnight to afford the title compound as a light tan solid, 4.89 g (50% yield), identified by NMR and mass spectral analyses. 1H NMR (500 MHz, CDCl3) δ 10.58 (br s, 1H), 8.73 (t, J=1.8 Hz, 1H), 8.61 (dt, J=7.8, 1.2 Hz, 1H), 7.75-7.72 (m, 1H), 7.42-7.38 (m, 2H), 7.32 (s, 1H); ESI MS m/z 250 [C10H7BrN2O+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. temperaturecooled to room temperature
  4. temperaturefurther cooled with an ice bath for 1 h
  5. filtrationfiltered
  6. washThe filtercake is washed with water
  7. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-a3362c9b49314105acb1741a2cb14a8b
Source dataset
uspto-grants-2008_11
Patent number
US07456186B2

Reaction notes

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