Benzyl Bromide → HCID 10828858, Verbindung

HRID 263895

Reaktionsgleichung

Reaktionsgleichung von HRID 263895
[Cl:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC#N>[CH2:19]([N:6]1[C:5]2[CH:7]=[C:8]([Cl:12])[C:9]([Cl:11])=[CH:10][C:4]=2[N:3]=[C:2]1[Cl:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2860092,5,6-Trichloro-1H-benzimidazole

Produkt 1

HCID 10828858HCID 10828858, VerbindungAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2,5,6-trichlorobenzimidazole (5, 50 mg, 0.0002 moles) was dissolved in 15 ml of CH3CN, and K2CO3 (33 mg, 0.0002 moles) was added. The mixture was stirred at room temperature for one hour, at which time benzyl bromide (0.024 ml, 0.0002 moles) was added. The mixture was then stirred for two days. TLC analysis showed the formation of a new compound with a higher Rf than staffing material. The mixture was then concentrated and a liquid-liquid extraction was done using CHCl3, and H2O. The CHCl3 layer was kept, dried with MgSO4, filtered, and then concentrated. Column chromotograpy was then performed using 2% MeOH/CHCl3 to elute the compounds. The fractions were collected and those containing the compound were concentrated. The compound was recrystallized from MeOH, giving 60 mg of 1-benzyl-2,5,6-trichlorobenzimidazole (181) (96.2%). 1H NMR (CDCl3): d 3.49 ppm (s, 3H), 7.13 (m, 2H), 7.32 (m, 4H), 7.78 (s, 1H). 13C NMR (CDCl3): d 43.20 ppm, 106.25, 115.78, 121.62, 122.24, 122.66, 123.50, 124.15, 129.05, 129.16, 135.97, 137.68. GC-MS: m/e 310, 273, 239, 221,197, 170, 158, 138, 120, 100, 91, 77, 65, 51, 39. m.p: 175°-176° C. Elemental Analysts: (C14H9Cl3N2): Calculated: C, 53.85; H, 2.88; N, 8.97. Found: C, 53.92; H, 2.85; N, 8.89. UV imax nm (e×104): (pH 7) 263 (0.080), 290 (0.102), 299 (0.154); (pH 1) 224 (0.412), 258 (0.157), 290 (0.155), 299 (0.166).

Aufarbeitung

  1. additionwas added
  2. concentrationThe mixture was then concentrated
  3. extractiona liquid-liquid extraction
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washto elute the compounds
  8. customThe fractions were collected
  9. concentrationthose containing the compound were concentrated
  10. customThe compound was recrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-850c1fdc45d44fadaaaf3ad0896f69ad
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646125

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