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

HRID 926462

Reaction equation

HRID 926462 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, 15.1 mL, 45.2 mmol) was added dropwise, to a solution of 5-bromo-1-methyl-1H-imidazole (7.28 g, 45.2 mmol) in dry DCM (40 mL) at 0° C. and stirred for 10 minutes. The mixture was then stirred at room temperature for 30 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (8.45 g, 37.7 mmol, Intermediate 14: step a) dissolved in 22 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 18 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over MgSO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates were filtered and dried to provide the title compound.

Workup

  1. stirringThe mixture was then stirred at room temperature for 30 minutes
  2. temperaturecooled in an ice-brine bath
  3. additionwas added dropwise
  4. customA dark brown solid mass formed
  5. customThe ice bath was removed
  6. stirringmixture stirred at room temperature for 18 hours
  7. additionWater was added to the suspension
  8. additionMore DCM was added
  9. customlayers separated
  10. dry with materialThe organic layer was dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. additionEt2O was added
  14. customthe slurry sonicated
  15. customprecipitates
  16. filtrationwere filtered
  17. customdried

Sources & evidence

ORD record
ord-471c71399b724a55818a69da9684eabe
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Linked notes

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