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

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Reaction Steps

A procedure similar to that in Example 4 was used. 4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 6 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 (100:0-10:1) to obtain a product as a white solid in a yield of 60.8%, mp: 106-108└. 1H-NMR (CDCl3, 400 MHz) δ: 3.83 (3H, s, OCH3), 3.92 (3H, s, OCH3), 3.97 (3H, s, OCH3), 4.33 (2H, s, CH2), 6.85˜6.89 (3H, m, ArH), 7.37˜7.45 (6H, m, ArH), 8.18 (2H, t, J=8.68 Hz, ArH), 10.48 (1H, br, CONH, exchangable); EI-MS m/e (%): 505.0 (M+, 54), 165.0 (100); HREI-MS Calcd. for C26H23N3O6S: 505.1308. found: 505.1315. Anal. Calcd. for C26H23N3O6S: C, 61.77; H, 4.59; N, 8.31. found: C, 61.90; H, 4.70; N, 8.05.

Provenance & Evidence