반응 #730587

반응 방정식

p-TsOH.H2O

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

trimethyl orthobenzoate

→

title compound

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

용매

DCM

반응 조건

후처리

1. 1
   농축The reaction mixture was then concentrated in vacuo
2. 2
   기타to give a yellow solid which
3. 3
   기타was triturated with 40% MeOH/water (375 mL)
4. 4
   여과filtered
5. 5
   세척washed with saturated NaHCO3 (20 ml)+H2O (80 ml) twice
6. 6
   건조40% MeOH/H2O (2×50 ml), and dried

실험 절차

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+].

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