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

HRID 526838

Reaction equation

HRID 526838 reaction equation
Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][CH:3]=1.C([Mg]Br)C.CON(C)[C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:7][N:6]1[C:2]([C:15]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[O:25])=[CH:3][N:4]=[CH:5]1

Participants

5

Reactant 3

HCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 2991007N-methoxy-N-methyl-4-nitrobenzamideHCID 178418443HCID 178418443, compound

Product 1

HCID 86715600(1-Methyl-1H-imidazol-5-yl)(4-nitrophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.98 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.98 mmol, 3.0 M in diethyl ether) dropwise over a 10 minute period. The resulting orange-red solution was stirred at room temperature for 15 minutes, cooled in an ice bath to 0° C. and N-methoxy-N-methyl-4-nitrobenzamide (3.5 g, 16.65 mmol, Intermediate 7: step a) dissolved in DCM (10 mL) was added dropwise. The ice bath was removed and the solid suspension stirred at room temperature for 48 hours. Water was added followed by 6 M aqueous HCl to a neutral pH (pH=6-7). The aqueous mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated. Et2O was added and the mixture sonicated. The precipitate was collected by filtration and dried to provide the title compound as a tan solid.

Workup

  1. temperaturecooled in an ice bath to 0° C.
  2. additionwas added dropwise
  3. customThe ice bath was removed
  4. stirringthe solid suspension stirred at room temperature for 48 hours
  5. additionWater was added
  6. extractionThe aqueous mixture was extracted with DCM
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionEt2O was added
  11. customthe mixture sonicated
  12. filtrationThe precipitate was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-b41eba38d3cc48979088abf09e668c45
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Linked notes

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