反応 #730587

反応方程式

p-TsOH.H2O

N1-benzyl-4-bromobenzene-1,2-diamine

trimethyl orthobenzoate

→

title compound

1-Benzyl-5-bromo-2-phenyl-1H-benzimidazole

溶媒

DCM

反応条件

後処理

1. 1
   濃縮The reaction mixture was then concentrated in vacuo
2. 2
   その他to give a yellow solid which
3. 3
   その他was triturated with 40% MeOH/water (375 mL)
4. 4
   ろ過filtered
5. 5
   洗浄washed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice
6. 6
   乾燥40% MeOH/H2O (2×50 ml), and dried

実験手順

p-TsOH.H2O (311.7 mg, 1.606 mmol) was added to a DCM (50 ml) solution of N1-benzyl-4-bromobenzene-1,2-diamine (4451 mg, 16.06 mmol) and trimethyl orthobenzoate (3096 μl, 17.66 mmol) and the resulting mixture was stirred at rt under an atmosphere of Nitrogen for 40 h. The reaction mixture was then concentrated in vacuo to give a yellow solid which was triturated with 40% MeOH/water (375 mL), filtered, washed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice and 40% MeOH/H2O (2×50 ml), and dried to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm=5.44 (s, 2H), 7.05-7.08 (m, 3H), 7.30-7.36 (m, 4H), 7.44-7.50 (m, 3H), 7.66-7.68 (m, 2H) and 7.99 (dd, 1H, J=0.4 & 1.6 Hz). MS(ES+): m/z 363.20 and 365.26[MH+].

出典