Reaktion #1285025

Reaktionsgleichung

methyl (±)-[5- [chloro (phenyl)methyl]-1H-benzimidazol-2-yl]carbamate

ammonium hydroxide

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title product

Ausbeute 22.0%

Methyl (±)-[5-[Amino (Phenyl)Methyl]-1H-Benzimidazol-2-yl]Carbamate

Ausbeute 22.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   SonstigeThe solvent was then removed
3. 3
   Sonstigethe residue was chromatographed on silica gel 60F254 (40 g, 70-230 mesh, column size 1'×1")
4. 4
   EinengenFractions 3 through 12 (20 mL each) upon concentrating on a steam bath under vacuum

Vorschrift

The above hydrochloride salt of methyl (±)-[5- [chloro (phenyl)methyl]-1H-benzimidazol-2-yl]carbamate was then suspended in dry tetrahydrofuran (30 mL) and excess ammonium hydroxide was added to this suspension. The resulting reaction mixture was stirred at room temperature for 12 hours. The solvent was then removed and the residue was chromatographed on silica gel 60F254 (40 g, 70-230 mesh, column size 1'×1") using CHCl3 :CH3OH (95:5) as eluant. Fractions 3 through 12 (20 mL each) upon concentrating on a steam bath under vacuum afforded the title product, yield 22%; mp>232° C.; IR (KBr): 3340, 1718, 1630, 1600, 870, 750, 721, 695 cm-1. 1H-NMR (DMSO-d6): δ 3.75 (2, 3H, --OCH3); 5.23 (2, 1H, CH--N), 5.60-6.87 (m, 2H, NH2 [exchangeable with D2O]), 6.90-7.83 (m, 9H, Ar--H and NHCO [exchangeable with D2O]). Analysis calculated for C16H16N4O2 : C, 64.85; H, 5.44; N, 18.91 and found: C, 65.03; H, 5.53; N, 18.67.

Quelle