METHOD OF PRODUCING PHENYLISOXAZOLINE COMPOUND Russian patent published in 2024 - IPC C07D413/10 C07D239/54 

FIELD: chemistry.

SUBSTANCE: invention relates to a method for synthesis of a phenylisoxazoline compound, characterized by that it involves: 1) use of 2-fluoro-4-chloro-5-methylaniline and a chloroformate compound as starting substances for the reaction to obtain a carbamate compound, wherein 2-fluoro-4-chloro-5-methylaniline is heated to 60–100 °C in a solvent and under alkaline conditions and a chloroformate compound is added dropwise, where the molar ratio of 2-fluoro-4-chloro-5-methylaniline (I), alkali and chloroformate compound is 1:(1–4):(1–2); 2) reacting the carbamate obtained at step 1) with 3-amino-4,4,4-trifluorocrotonate in a solvent and under alkaline conditions with catalyst at 100–140 °C, followed by methylation with a methylating reagent to obtain uracil, wherein the molar ratio of carbamate (II), 3-amino-4,4,4-trifluorocrotonate, alkali, catalyst and methylating reagent is 1:(1–1.2):(1.5–3):(0.01–0.1):(1–2); 3) treatment of uracil obtained in step 2) by oxidation or dihalogenation of hydrolysis to obtain uracilbenzaldehyde, wherein halogenated reagent, solvent and catalyst are mixed for reaction at 50–150 °C; then the temperature is lowered to room temperature and extraction is carried out to collect the organic phase; adding acid for hydrolysis; where molar ratio of uracil (III), halogenated reagent, catalyst and acid is 1:(2.5–3.5):(0.01–0.1):(10-30); 4) reaction of uracilbenzaldehyde (IV) obtained in step 3) with hydroxylamine hydrochloride to obtain uracilbenzaldoxime, wherein uracilbenzaldehyde (IV) reacts with hydroxylamine hydrochloride in alcohol at room temperature to obtain uracylbenzaldoxime (V), where the molar ratio of uracilbenzaldehyde (IV) to hydroxylamine hydrochloride is 1:(1-1.5); 5) chlorination of NCS of uracilbenzaldoxime obtained in step 4), followed by cyclisation with an alkene compound to obtain a phenylisoxazoline compound, wherein uracilbenzaldoxime (V) obtained in step 4), added to a solvent; halogenated reagent is added at 20–40 °C, and alkene compound (VI) and alkali are added at this temperature; where the molar ratio of uracilbenzaldoxime (V), halogenated reagent, alkene compound (VI) and alkali is 1:(1–1.5):1:(1–2), wherein the synthesis path is as follows:

R1 is selected from methyl or ethyl; R2 is selected from hydrogen, C1-C4 alkyl or CO2R4; R3 is selected from hydrogen, C1-C4 alkyl or C1-C4 haloalkyl; R4 is selected from C1-C4 alkyl or C1-C4 haloalkyl.

EFFECT: method enables to obtain a phenylisoxazoline compound with cheap and readily available raw material and a simple synthesis process.

9 cl, 1 tbl, 2 ex