Water → 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole

HRID 1622460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622460
[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[C:17]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[C:17]=3[CH3:26])[C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27756171-(Bromomethyl)-2-methyl-3-(trifluoromethyl)benzeneHCID 532566897-Bromo-5-nitro-1H-benzimidazole

Produkt 1

HCID 866878234-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazoleAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Into a 250 mL round bottomed flask charged with 4-bromo-6-nitro-1H-benzo[d]imidazole (5 g, 20.66 mmol) in N,N-Dimethylformamide (DMF) (100 mL) was added 1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene (7.84 g, 31.0 mmol) and potassium carbonate (8.57 g, 62.0 mmol). The resulting reaction mixture was stirred 1 h at 60° C., cooled to room temperature and poured into water, extracted with ethyl acetate, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified on a silica gel cartridge and eluted with a gradient of 0% ethyl acetate/hexanes to 80% over 10 column volumes. The expected compound was collected and evaporated to yield 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (2.58 g, 6.23 mmol, 30.2% yield) as a tan solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.47 (s, 3H) 5.52 (s, 2H) 7.02 (d, J=7.58 Hz, 1H) 7.27-7.37 (m, 1H) 7.72 (d, J=8.08 Hz, 1H) 8.12 (s, 1H) 8.25 (d, J=2.02 Hz, 1H) 8.48 (d, 1H); LC/MS: MS (ES+) m/e 415 [M+H]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified on a silica gel cartridge
  8. washeluted with a gradient of 0% ethyl acetate/hexanes to 80% over 10 column volumes
  9. customThe expected compound was collected
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c0272dec4c93496ba077ffe58ed553f5
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778937B2

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