5-Bromo-1-methyl-1H-imidazole → (1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone

HRID 928780

Reaction equation

HRID 928780 reaction equation
CC[Mg+].[Br-].Br[C:6]1[N:10]([CH3:11])[CH:9]=[N:8][CH:7]=1.CON(C)[C:15](=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=1>C(Cl)Cl>[CH3:11][N:10]1[C:6]([C:15]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=2)=[O:26])=[CH:7][N:8]=[CH:9]1

Participants

5

Reactant 3

HCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 46318653N-methoxy-N,3-dimethyl-4-nitrobenzamideHCID 178461630HCID 178461630, compound

Product 1

HCID 86715615(1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.689 mmol) was added dropwise, over a 25 minutes period, to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.689 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.408 mmol, Intermediate 40: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates filtered to provide the title compound as a tan solid.

Workup

  1. temperaturecooled in an ice-brine bath
  2. additionwas added dropwise
  3. customA dark brown solid mass formed
  4. customThe ice bath was removed
  5. stirringmixture stirred at room temperature for 48 hours
  6. additionWater was added to the suspension
  7. additionMore DCM was added
  8. customlayers separated
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. additionEt2O was added
  13. customthe slurry sonicated
  14. customprecipitates
  15. filtrationfiltered

Sources & evidence

ORD record
ord-9a724315f22247e3bbcbfd7715bfbb9e
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Linked notes

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