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US 12,606,547 B2Granted
Preparation method of phenylisoxazoline compound
AssigneesShenyang Sinochem Agrochemicals R&D Co., Ltd., Jiangsu Yangnong Chemical Co., Ltd.
InventorsJichun Yang, Aiying Guan, Qiao Wu, Enming Wu, Gongxin Wu, Changling Liu
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Abstract
In a synthesis method of a phenylisoxazoline compound 2-fluoro-4-chloro-5-methylaniline is used as starting material for firstly synthesizing a uracil ring, and then synthesizing an isooxazoline ring to obtain a target compound, phenylisoxazoline compound (VII), as shown in the reaction pathway below. The preparation method can be used for the synthesis of phenylisoxazoline containing uracil.
Claims8
A synthesis method of a phenylisoxazoline compound, comprising:
- 1) reacting 2-fluoro-4-chloro-5-methylaniline (I) and a chloroformate compound to obtain a carbamate compound (II);
- 2) reacting the carbamate compound (II) with 3-amino-4,4,4-trifluorocrotonate, followed by methylation with a methylating reagent to obtain uracil (III);
- 3) processing uracil (III) by oxidization or dihalogenation hydrolysis to obtain uracil benzaldehyde (IV);
- 4) reacting the uracil benzaldehyde (IV) with hydroxylamine hydrochloride to obtain uracil benzaldoxime (V);
- and
- 5) conducting N-chlorosuccinimide (NCS) chlorination on the uracil benzaldoxime (V), followed by cyclization with an alkene compound (VI) to obtain the phenylisoxazoline compound (VII),
- wherein,
- R1 is methyl, ethyl, phenyl, 4-nitrophenyl, or benzyl;
- R2 is hydrogen, C1-C4 alkyl, CO2R4, or CH2ORs;
- R3 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, CO2R4, or CH2OR5;
- R4 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkyl, C1-C4alkoxy C1-C4 alkyl, C1-C4 alkylcarbonyl oxy C2-C3 alkyl, unsubstituted benzyl, unsubstituted furan methylene, unsubstituted tetrahydrofuran methylene, substituted benzyl, substituted furan methylene, and substituted tetrahydrofuran methylene that are substituted by 1-4 substituents independently selected from halogen, CN, NO2, C1-C4 alkyl, and C1-C4 haloalkyl;
- and
- R5 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy carbonyl, C1-C4 alkyl carbonyl, C1-C4 haloalkyl carbonyl, C3-C6 cycloalkyl carbonyl, C3-C6 halocycloalkyl carbonyl, C1-C4 alkyl sulfonyl, C1-C4 halo alkyl sulfonyl, C1-C3 alkyl aminosulfonyl, di(C1-C3) alkyl aminosulfonyl, C1-C3 alkyl aminocarbonyl, di(C1-C3) alkyl aminocarbonyl, di(C1-C3)alkyl aminothiocarbonyl, C1-C2 alkylsulfuryl C2-C4 alkyl carbonyl, phenyl C1-C2 alkyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenyl C2-C4 alkyl carbonyl, phenoxy C1-C2 alkyl carbonyl, thiophenyl carbonyl, pyrazole carbonyl, and quinoline carbonyl, which are unsubstituted or substituted by 1-4 substituents independently selected from the group consisting of halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy carbonyl, C1-C4 alkyl, C1-C4 alkyl sulfonyl, and
- phenoxy which is independently substituted by 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
11 more elements
A synthesis method of a phenylisoxazoline compound, comprising:
- chlorinating uracil benzaldoxime (V) using N-chlorosuccinimide (NCS) to obtain the compound of formula V;
- and
- cyclization with the compound of formula V with an alkene compound (VI) to obtain the phenylisoxazoline compound (VII):
- wherein,
- R2 is hydrogen, C1-C4 alkyl, CO2R4, or CH2OR5;
- R3 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, CO2R4, or CH2OR5;
- R4 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 alkenyl, C3-C4 alkyl, C1-C4alkoxy C1-C4 alkyl, C1-C4 alkylcarbonyl oxy C2-C3 alkyl, unsubstituted benzyl, unsubstituted furan methylene, unsubstituted tetrahydrofuran methylene, substituted benzyl, substituted furan methylene, and substituted tetrahydrofuran methylene that are substituted by 1-4 substituents independently selected from halogen, CN, NO2, C1-C4 alkyl, and C1-C4 haloalkyl;
- and
- R5 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy carbonyl, C1-C4 alkyl carbonyl, C1-C4 haloalkyl carbonyl, C3-C6 cycloalkyl carbonyl, C3-C6 halocycloalkyl carbonyl, C1-C4 alkyl sulfonyl, C1-C4 halo alkyl sulfonyl, C1-C3 alkyl aminosulfonyl, di(C1-C3) alkyl aminosulfonyl, C1-C3 alkyl aminocarbonyl, di(C1-C3) alkyl aminocarbonyl, di(C1-C3)alkyl aminothiocarbonyl, C1-C2 alkylsulfuryl C2-C4 alkyl carbonyl, phenyl C1-C2 alkyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenyl C2-C4 alkyl carbonyl, phenoxy C1-C2 alkyl carbonyl, thiophenyl carbonyl, pyrazole carbonyl, and quinoline carbonyl, which are unsubstituted or substituted by 1-4 substituents independently selected from the group consisting of halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy carbonyl, C1-C4 alkyl, C1-C4 alkyl sulfonyl, and
- phenoxy which is independently substituted by 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy.
7 more elements
Dependencies are inferred from the claim text.