3,5-Difluorobenzoyl chloride → 3,5-difluoro-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 3,5-difluorobenzoyl chloride prepared in the step 1 of Example 16 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 66.7%, mp: 189-190└. 1H-NMR (CDCl3, 400 MHz) δ: 3.76 (3H, s, OCH3), 4.34 (2H, s, CH2), 6.72 (2H, d, J=8.68 Hz, ArH), 6.85 (1H, t, 3JFH=8.40 Hz, ArH), 7.18 (2H, d, 3JFH=5.32 Hz, ArH), 7.25 (2H, d, J=8.68 Hz, ArH), 7.40 (2H, d, J=8.40 Hz, ArH), 8.21 (2H, d, J=8.40 Hz, ArH), 12.05 (1H, br, CONH); EI-MS m/e (%): 481.1 (M+, 100), 141.0 (63); HREI-MS Calcd. for C24H17F2N3O4S: 481.0908. found: 481.0902. Anal. Calcd. for C24H17F2N3O4S: C, 59.87; H, 3.56; N, 8.73. found: C, 59.98; H, 3.80; N, 8.67.

Provenance & Evidence