Undecanoic Acid → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethyl undecanoate

Beteiligte Stoffe

Reaktionsschritte

To a solution of the compound 22 (345 mg, 1 mmol), undecanoic acid (186 mg, 1 mmol) and N,N-dimethylaminopyridine (122 mg, 1 mmol) in methylene chloride (3 mL) was added 1,3-dihexylcarbodiimide (206 mg, 1 mmol) under ice-cooling, and stirred at room temperature overnight. The precipitated insoluble matter was filtered, and the filtrate was concentrated. The residue was purified by chromatography on a silica gel column (hexane - ethyl acetate (1:1)) to give the compound 106 (461 mg, 90%) as oil. Rf 0.50 (1:1 EtOAc - hexane). 1H-NMR (CDCl3): δH0.88 (3 H, S, t-like, CH3), 1.23 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.25 (14 H, bs, --CH2 --), 3.09 (1 H, sep, J 6.9 Hz, (CH3)2CH), 3.10 (2 H, t, J 7.2 Hz, CH2), 3.49 (3 H, s, NCH3), 4.42 (2 H, t, J 7.2 Hz), 6.80 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 7.11 (1 H, t, J 1.8 Hz, arom 4-H) Elementary analysis (for C26H38N2O2SCl2) Calcd. : C, 60.81% H, 7.46% N, 5.45% S, 6.24% Cl, 13.81% Found: C, 60.55% H, 7.39% N, 5.54% S, 6.14% Cl, 13.81%

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