反应详情

Five grams (24.1 mmol) of N-phenyl-2,2,2-trifluoroacetimidoyl chloride obtained in Example 1, 2.83 g (43.4 mmol) of sodium azide, 1.66 g (12.1 mmol) of triethylamine hydrochloride, and 40 ml of toluene were introduced into a 100 ml flask and reacted at 80° C. for 16.5 hours. After the reaction, the reaction solution was cooled to room temperature and washed with water (30 ml×3). The organic phase was dried over anhydrous magnesium sulfate for 1 hour, filtered, and then subjected to solvent removal by evaporation. The crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7), resulting in 4.81 g of 1-phenyl-5-(trifluoromethyl)-1H-tetrazole as a pale yellow oil (yield: 93.2%). IR (neat, cm−1): 3071, 1531, 1499, 1312, 1207, 1167, 1013, 766, 691 1H-NMR (CDCl3): δ 7.60-7.54 (m, 3H), 7.38 (d, J=8.7 Hz, 2H), 7.06 (d, J=8.7 Hz, 2H), 3.89 (s, 3H) 13C-NMR (CDCl3): δ 145.90 (q, J=42.0 Hz), 132.41, 131.59, 131.58, 129.79, 129.76, 125.05, 117.73 (q, J=270.0 Hz) Elemental analysis: Value calculated for C8H5F3N4: C, 44.87%; H, 2.35%; N, 26.16% Value found: C, 44.27%; H, 2.24%; N, 25.95% Decomposition temperature (DSC): 290° C. (1.17 kJ/g), 367° C. (1.55 kJ/g)

1. customreacted at 80° C. for 16.5 hours
2. customAfter the reaction
3. washwashed with water (30 ml×3)
4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate for 1 hour
5. filtrationfiltered
6. customsubjected to solvent removal by evaporation
7. customThe crude product thus obtained
8. customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)