Chlorosuccinimide → HCID 23139479, compound

Participants

Reaction Conditions

Reaction Steps

NCS (0.05 g, 0.37 mmol, 1.1 eq.) dissolved in DMF (⅔ mL) was added drop wise to a stirred solution of 5-(2-methoxy-5-nitro-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole, see Example 1.99 (0.1 g, 0.33 mmol) in DMF (1⅓ mL) at 0° C. The reaction mixture was stirred 0° C. and TLC indicated no product. An additional equivalent of NCS was added and the reaction mixture was stirred at 80° C. overnight which resulted in completion of the reaction. The DMF was removed under vacuum and the crude mixture was diluted with EtOAc (50 mL) and washed with brine (3×10 mL). The EtOAc phase was dried over anhydrous MgSO4, filtered and evaporated to give the partially purified product 4-chloro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole (0.13 g) as a light yellow solid: LCMS m/z (%)=336 (M+H35Cl, 100), 382 (M+H37Cl, 33). 1H NMR (400 MHz, CDCl3) δ: 8.37 (dd, J=8.0, 4.0 Hz, 1H), 8.16 (d, J=4.0 Hz 1H), 7.09 (d, J=8.0 Hz, 1H), 3.92 (s, 3H), 3.69 (s, 3H).

Provenance & Evidence