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

HRID 926466

Reaktionsgleichung

Reaktionsgleichung von HRID 926466
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-1-methyl-1H-imidazole (3.22 g, 19.982 mmol) in DCM (15 mL) was added ethyl magnesium bromide (6.66 mL, 19.982 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, 16.652 mmol, Intermediate 15: step a) dissolved in DCM (10 mL) was added dropwise. The cold 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.

Aufarbeitung

  1. temperaturecooled in an ice bath to 0° C.
  2. additionwas added dropwise
  3. customThe cold 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

Quellen und Nachweise

ORD-Eintrag
ord-3316d5b31bb1458ca8ed13c3a4f7b56e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284308B2

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