Water → 5-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrile

HRID 1786178Notes

Reaction equation

HRID 1786178 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:15]2[CH:16]=[C:12]([CH3:11])[N:13]=[CH:14]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27249005-Bromo-2-fluorobenzonitrileHCID 178418800HCID 178418800, compound

Product 1

HCID 669615175-bromo-2-(4-methyl-1H-imidazol-1-yl)benzonitrileYield 59.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-2-fluorobenzonitrile (25.0 g, 125 mmol), 4-methylimidazole (12.5 g, 152 mmol), potassium carbonate (34.55 g, 250 mmol) in DMSO (500 mL) was stirred at 90° C. for 16 h. Water (1.5 L) was added and the resulting suspension was stirred with ice-bath cooling for 1 h. The precipitate was then filtered off, washed with water (0.5 L) and dried at 50° C. over KOH. The resulting raw material (25.6 g) was dissolved in boiling ethyl acetate (300 mL). After addition of diisopropylether (300 mL) the solution was allowed to cool to room temperature. Filtration and drying afforded the title compound (19.35 g, 59%) as a white solid. Mp 166° C.

Workup

  1. stirringthe resulting suspension was stirred with ice-bath
  2. temperaturecooling for 1 h
  3. filtrationThe precipitate was then filtered off
  4. washwashed with water (0.5 L)
  5. dry with materialdried at 50° C. over KOH
  6. dissolutionThe resulting raw material (25.6 g) was dissolved
  7. additionAfter addition of diisopropylether (300 mL) the solution
  8. temperatureto cool to room temperature
  9. filtrationFiltration
  10. customdrying

Sources & evidence

ORD record
ord-def137155da94eccaf1fd18f4c149956
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

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