[2-(trifluoromethyl)phenyl]hydrazine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6.1 g (22 mmol) of ethyl N-acetyl-2-chloro-4-fluorobenzimidate and 6.7 g (25 mmol) of o-trifluoromethylphenylhydrazine hydrochloride in 100 ml of toluene is treated with 3.9 ml (28 mmol) of triethylamine and the whole is heated at reflux temperature for 18 hours. Thereafter, the reaction mixture is washed once with water and extracted twice with 50 ml of concentrated hydrochloric acid. The acidic aqueous phases are neutralized with ice-cold sodium hydroxide solution and extracted twice with diethyl ether, and the combined extracts are dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is subjected to a bulb-tube distillation, the fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected and finally crystallized from diisopropyl ether/n-hexane. In this manner there is obtained 3-(2-chloro-4-fluorophenyl)-5-methyl-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole, m.p. 116° C.; 1H--NMR (CDCl3, 60 MHz): 2.37 (s,CH3); mass spectrum: 335 (48), 314(43), 159(100). the whole is heated at reflux temperature for 18 hours Thereafter, the reaction mixture is washed once with water extracted twice with 50 ml of concentrated hydrochloric acid extracted twice with diethyl ether the combined extracts are dried over anhydrous magnesium sulfate evaporated under reduced pressure The residue is subjected to a bulb-tube distillation the fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected finally crystallized from diisopropyl ether/n-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6.1 g (22 mmol) of ethyl N-acetyl-2-chloro-4-fluorobenzimidate and 6.7 g (25 mmol) of o-trifluoromethylphenylhydrazine hydrochloride in 100 ml of toluene is treated with 3.9 ml (28 mmol) of triethylamine and the whole is heated at reflux temperature for 18 hours. Thereafter, the reaction mixture is washed once with water and extracted twice with 50 ml of concentrated hydrochloric acid. The acidic aqueous phases are neutralized with ice-cold sodium hydroxide solution and extracted twice with diethyl ether, and the combined extracts are dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is subjected to a bulb-tube distillation, the fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected and finally crystallized from diisopropyl ether/n-hexane. In this manner there is obtained 3-(2-chloro-4-fluorophenyl)-5-methyl-1-(α,α,α-trifluoro-o-tolyl)-1H-1,2,4-triazole, m.p. 116° C.; 1H--NMR (CDCl3, 60 MHz): 2.37 (s,CH3); mass spectrum: 335 (48), 314(43), 159(100). the whole is heated at reflux temperature for 18 hours Thereafter, the reaction mixture is washed once with water extracted twice with 50 ml of concentrated hydrochloric acid extracted twice with diethyl ether the combined extracts are dried over anhydrous magnesium sulfate evaporated under reduced pressure The residue is subjected to a bulb-tube distillation the fractions with b.p. 200° C./0.01 mmHg (9.33 Pa) being collected finally crystallized from diisopropyl ether/n-hexane

Conditions: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13.6 g (98 mmol) of potassium carbonate in 70 ml of water are added at 10° C. while stirring to a suspension of 10.4 g (49 mmol) of α,α,α-trifluoro-o-tolylhydrazine hydrochloride in 50 ml of ethyl acetate. 7.8 g (49 mmol) of 2,6-difluorobenzoyl fluoride are subsequently added dropwise to the clear solution while cooling so that the internal temperature is maintained at 3° C. The mixture is stirred at 5° C. for 60 minutes and thereafter at 25° C. for 4 hours, and the organic phase is separated. The aqueous phase is back-extracted with 50 ml of ethyl acetate and subsequently treated with 1.85 g (25 mmol) of calcium hydroxide in order to precipitate the calcium fluoride. The combined organic phases are washed in each case once with dilute hydrochloric acid and sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After recrystallization from acetone and n-hexane there is obtained 2,6-difluoro-N' -(α,α,α-trifluoro-o-tolyl)-benzhydrazide as a white crystallizate, m.p. 129°-130° C.; mass spectrum m/e: M+ 316(26), 141(100). while cooling so that the internal temperature at 25° C. for 4 hours the organic phase is separated The aqueous phase is back-extracted with 50 ml of ethyl acetate to precipitate the calcium fluoride The combined organic phases are washed in each case once with dilute hydrochloric acid and sodium bicarbonate solution dried over anhydrous magnesium sulfate evaporated under reduced pressure After recrystallization from acetone and n-hexane