반응 #9055

반응 방정식

2,3-diaminotoluene

trimethylorthoformate

trifluoroacetic acid

→

4-methyl-1H-benzimidazole

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   세척washed consecutively with saturated aqueous NaHCO3 (40 mL) and H2O (40 mL)
2. 2
   건조The combined organic extracts were dried over MgSO4
3. 3
   농축concentrated to a rusty brown solid (1.07 g, 97%)

실험 절차

To a stirred solution of 2,3-diaminotoluene (1.00 g, 8.2 mmol) in CH2Cl2 (82 mL) was added trimethylorthoformate (4.5 mL, 41 mmol) and trifluoroacetic acid (0.32 mL, 4.1 mmol) and the mixture stirred at room temperature for 24 h after which the reaction mixture was diluted with CH2Cl2 (200 mL), and washed consecutively with saturated aqueous NaHCO3 (40 mL) and H2O (40 mL). The aqueous layers were reextracted with CH2Cl2 (2×100 mL). The combined organic extracts were dried over MgSO4 and concentrated to a rusty brown solid (1.07 g, 97%). 1H NMR (300 MHz, CDCl3) δ 8.08 (s, 1H), 7.49 (d, 1H, J=8.1 Hz), 7.23–7.18 (m, 1H), 7.10 (d, 1H, J=7.5 Hz), 2.64 (s, 3H).

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