Dimethyl Sulfide → 4-Nitro-N'-(4-(trifluoromethoxy)phenyl)-benzohydrazonoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred solution of N-chlorosuccinimide (1.23 g, 9.22 mmoL) in CH2Cl2 (16 mL) at 0° C. was added dimethyl sulfide (1.36 mL, 18.45 mmoL) and the reaction mixture was stirred for 15 min and then cooled to −78° C. To this solution was added 1-(4-nitrobenzylidene)-2-(4-(trifluoromethoxy)-phenyl)hydrazine (2 g, 6.15 mmoL) dissolved in CH2Cl2 (16 mL) and the reaction mixture was stirred at this temperature for 1 h, warmed to room temperature and stirred for 2 h. The solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (15 mL) and added to a SiO2 loading cartridge and purified via flash column chromatography (Gradient EtOAc/hexanes). The title compound was isolated as a yellow solid: mp 172-175° C.; 1H NMR (400 MHz, CDCl3) δ 8.29-8.26 (m, 3H), 8.09-8.05 (m, 3H), 7.22 (s, 4H); 19F NMR (376 MHz, CDCl3) δ −58.30; ESIMS m/z 359 ([M+H])+.

Provenance & Evidence