Dimethylformamide → HCID 58524127, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-methyl-6-methoxycarbonylbenzotriazole-4-carbaldehyde oxime (0.1 g) in dimethyl formamide (10 ml) was treated with N-chlorosuccinimide (0.17 g) and stirred at 40° C. for 2 h under nitrogen atmosphere. Then reaction mixture was cooled to room temperature and treated with 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (0.47 g) (prepared according to WO 2005/085216) and triethylamine (0.02 ml), stirred at room temperature for 16 h under nitrogen atmosphere, and treated with water (50 ml). The mixture was extracted with ethyl acetate (3×10 ml) and the combined organic layers were dried over sodium sulfate. Evaporation of solvents and purification by column chromatograph gave 3-methyl-4-methoxycarbonyl-7-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzotriazole (85 mg). 1H-NMR (400 MHz, CDCl3): 8.15 (d, 1H), 8.05 (d, 1H), 7.58 (d, 2H), 7.42 (t, 1H), 4.74 (bd, 1H), 4.60 (s, 1H), 4.38 (bd, 1H), 4.02 (s, 3H). LC-MS: m/z=472.96 (M+H).

Provenance & Evidence