O.[NH2:2][NH2:3].C(O)C.[F:7][C:8]([F:15])([CH3:14])[C:9](OCC)=O.C(S[C:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C>C(O)CCC>[F:15][C:8]([C:9]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:3][N:2]=1)([F:7])[CH3:14]
Next, 0.54 g (11 mmol) of hydrazine monohydrate and 10 mL of ethanol were put in a 100 mL three-neck flask and stirred at −10° C. for 15 minutes. Then, 1.5 g (11 mmol) of ethyl 2,2-difluoropropionate was dripped to this mixed solution at −10° C. little by little, and the solution was stirred for 48 hours while the temperature was increased to room temperature. Then, 2.6 g (11 mmol) of N-[(ethylsulfanyl)phenylmethylidene]aniline prepared in Step 1 and 20 mL of 1-butanol were added to this mixed solution, and the mixed solution was refluxed at 110° C. for 8 hours. After the reflux, the solvent was distilled off under a reduced pressure to give an oily substance. The given oily substance was purified by silica gel column chromatography. As developing solvents, first, toluene was used, and then ethyl acetate was used. The obtained fraction was concentrated to give a solid. This solid was recrystallized from a mixed solvent of ethanol and hexane, so that 3-(1,1-difluoroethyl)-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMCF2ptz) was prepared (a white solid, yield: 27%). The synthesis scheme of Step 2 is shown by (b-1).
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