Trifluoroacetic acid → 4-Methylbenzimidazole

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).

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

ORDレコード

ord-e0ceb6c6c9294af3b9f2df97c423d212

出典データセット

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07807694B2