Veratroyl chloride → N-[4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide

Participants

Reaction Steps

A procedure similar to that in Example 4 was used. 4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 9 and 3,4-dimethoxy-benzoyl chloride prepared in the step 1 of Example 12 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1) to obtain a product as a white solid in a yield of 24.0%, mp: 128-129└. 1H-NMR (DMSO-d6, 400 MHz) δ: 3.91 (3H, s, OCH3), 3.95 (3H, s, OCH3), 4.31 (2H, s, CH2), 6.90 (1H, d, J=9.00 Hz, ArH), 7.08 (2H, t, J=8.68 Hz, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 7.25˜7.47 (4H, m, ArH), 8.19 (2H, d, J=8.68 Hz, ArH), 10.04 (1H, br, CONH); EI-MS m/e (%): 493.2 (M+, 17), 165.3 (100); HREI-MS Calcd. for C25H20FN3O5S: 493.1108. found: 493.1105.

Provenance & Evidence