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

HRID 1507310

Reaction equation

HRID 1507310 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, 25.69 mmol) was added dropwise, over a 25 minute period to a solution of 5-bromo-1-methyl-1H-imidazole (4.1 g, 25.69 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, 21.41 mmol. Intermediate 13: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and the mixture stirred at room temperature for 48 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 the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and the 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. stirringthe mixture stirred at room temperature for 48 hours
  6. additionWater was added to the suspension
  7. additionMore DCM was added
  8. customthe layers were separated
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. additionEt2O was added
  13. customthe slurry sonicated
  14. filtrationthe precipitates filtered

Sources & evidence

ORD record
ord-841b15bbce4941b98c52ed10e7237997
Source dataset
uspto-grants-2015_12
Patent number
US09221804B2

Linked notes

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