反应详情

To a solution of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (2.09 g, 6.9 mmol) (prepared according to EP 1,006,102) in dichloromethane (30 ml) under stirring at 25° C., was added sequentially pyridine (0.8 ml, 9.9 mmol) and a solution of 3-sulfinylamino-benzoyl chloride (1.39 g, 6.9 mmol) (Example 1.1) in dichloromethane (7 ml). The reaction mixture was stirred at ambient temperature for 6 hours. The reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml) and stirred vigorously for 20 minutes. The mixture was diluted with water (20 ml) and the phases separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2). After evaporation of the solvents, the yellow oil was triturated with hexane, where it crystallized. The desired compound was isolated as white crystals. M.p. 143-145° C. 1H-NMR as described for Example 3.1.

1. customThe reaction mixture was quenched by addition of aqueous hydrochloric acid (2N) (4 ml)
2. stirringstirred vigorously for 20 minutes
3. additionThe mixture was diluted with water (20 ml)
4. customthe phases separated
5. extractionThe aqueous phase was extracted twice with ethyl acetate
6. washThe combined organic phases were washed successively with aqueous sodium hydrogen carbonate (saturated) and brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:4 to 3:2)
10. customAfter evaporation of the solvents
11. customthe yellow oil was triturated with hexane, where it
12. customcrystallized