4-Chloro-2-methoxy-6-methylaniline → 7-Bromo-N-(4-chloro-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698542
[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=O)[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[C:17]([NH2:18])=[C:16]([O:22][CH3:23])[CH:15]=1>CN1CCCC1=O.ClCCl>[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9]([NH:18][C:17]3[C:19]([CH3:21])=[CH:20][C:14]([Cl:13])=[CH:15][C:16]=3[O:22][CH3:23])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 591919724-Chloro-2-methoxy-6-methylanilineHCID 596354707-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Produkt 1

HCID 672728817-Bromo-N-(4-chloro-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazol-2-amineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 7-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 2.32 g (9.69 mmol) and 4-chloro-2-methoxy-6-methylaniline 4.98 g (29.1 mmol) in 0.5 mL of N-methyl-2-pyrrolidone was heated at 110° C. for 2 days. The reaction was cooled to room temperature and diluted with dichloromethane. The mixture was washed with sodium bicarbonate and water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate/hexane (1:1) to give 3.13 g (8.23 mmol, 85%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washThe mixture was washed with sodium bicarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with ethyl acetate/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-36d63c97986b4ce3bc5c281d2e673b11
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163935B2

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