4-Cyanobenzoyl chloride → 4-cyano-N-[4-(4-methoxy-phenyl)-5-(4-nitro-benzyl)-thiazol-2-yl]-benzamide

Participants

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 p-cyanobenzoyl chloride prepared in the step 1 of Example 13 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 yellow solid in a yield of 26.8%, mp: 190-192└. 1H-NMR (CDCl3, 400 MHz) δ: 3.80 (3H, s, OCH3), 4.32 (2H, s, CH2), 6.75 (2H, d, J=8.72 Hz, ArH), 7.25 (2H, d, J=8.68 Hz, ArH), 7.37 (2H, d, J=8.68 Hz, ArH), 7.59 (2H, d, J=8.40 Hz, ArH), 7.82 (2H, d, J=8.40 Hz, ArH), 8.19 (2H, d, J=8.72 Hz, ArH); EI-MS m/e (%): 470.1 (M+, 100), 130.0 (76); HREI-MS Calcd. for C25H18N4O4S: 470.1049. found: 470.1050. Anal. Calcd. for C25H18N4O4S: C, 63.82; H, 3.86; N, 11.91. found: C, 64.16; H, 3.68; N, 12.19.

Provenance & Evidence