Reaction Steps
A suspension of the above prepared 5-(3,5-dichlorophenylthio)-4-isopropyl-1-(4-pyridylmethyl)-1H-imidazol-2-ylmethyl carbamate (111) (219 mg, 0.5 mmol), di-n-butylamine (85 mg, 0.5 mmol) and paraformaldehyde (17.5 mg, 0.583 mmol) in ethyl acetate (3mL) was heated under reflux in an atmosphere of nitrogen for 5 days. After cooling down at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in a small amount of ether, and hexane was added thereto. The precipitated insoluble material was filtered off, and the filtrate was cooled at -50° C. The purified precipitate was collected to give the compound 112 (167 mg, 66%) as oil. 1H-NMR (CDCl3): δH 0.88 (6H, t, J 6.9 Hz, 2 x CH3), 1.31 (6 H, d, J 6.9 Hz, (CH3)2CH), 1.20-1.42 (8 H, m, 2 x --CH2 --), 2.34 (4 H, t, J 7.8 Hz, 2 x --CH2 --), 3.17 (1 H, sep, J 6.9 Hz, (CH3)2CH), 4.06 (2 H, d, J 6.0 Hz, NCH2NH), 4.82 (1 H, t, J 6.0 Hz, NCH2NH), 5.18 (2 H, s, CH2O), 5.24 (2 H, 8, NCH2), 6.68 (2 H, d, J 1.5 Hz, arom 2- and 6-H), 6.79 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.03 (1 H, t, J 1.5 Hz, arom 4-H), 8.42 (2 H, d-like, 4-pyridyl 3- and 5-H). Elementary analysis (C29H39N5O2SCl2) Calcd. : C, 58.78% H, 6.63% N, 11.82% S, 5.41% Cl, 11.96% Found: C, 58.72% H, 6.76% N, 11.63% S, 5.59% Cl, 11.63% hydrochloride of 112 Elementary analysis (for C29H39N6O2SCl5 3HCl 1.5H2O) Calcd. : C, 47.78% H, 6.22. N, 9.61% S, 4.40% Cl, 24.31% Found: C, 47.95% H, 6.01% N, 9.77% S, 4.63% Cl, 23.93%
