[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([NH:12][C:13](=O)[CH:14]=[N:15][O:16][CH3:17])=[C:4]([F:19])[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C1C=CC=CC=1.ClCCl>[CH3:17][O:16][N:15]=[CH:14][C:13](=[N:12][C:5]1[CH:6]=[C:7]([O:8][CH2:9][C:10]#[CH:11])[C:2]([Cl:1])=[CH:3][C:4]=1[F:19])[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1
0.42 g of the obtained N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamide was dissolved in 30 ml of benzene and after the addition of 0.36 g of phosphorus pentachloride, the resulting solution was refluxed for 4 hours. The concentrate obtained by concentrating the resulting reaction solution under reduced pressure was dissolved in 20 ml of dichloromethane and 0.32 g of pyrrolidine was added dropwise thereto at room temperature and the resultant solution was stirred at room temperature for 1 hour. The concentrate obtained by evaporating solvents from the resulting reaction solution under reduced pressure was purified by silica gel column chromatography to obtain 0.32 g of 2-(4-chloro-2-fluoro-5-propargyloxyphenylimino)-2-(pyrrolidine-1-yl)acetaldehyde O-methyloxime (1-5) (yield 64%). m.p. 73-75° C.
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